[ CAS No. 32779-38-7 ] {[proInfo.proName]}

Name: 32779-38-7|2-Chloro-5-iodopyrimidine|98%
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Quality Control of [ 32779-38-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 32779-38-7 ]

Product Details of [ 32779-38-7 ]

CAS No. :	32779-38-7	MDL No. :	MFCD06200210
Formula :	C₄H₂ClIN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WSZRCNZXKKTLQE-UHFFFAOYSA-N
M.W :	240.43	Pubchem ID :	1714223
Synonyms :

Calculated chemistry of [ 32779-38-7 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.76
TPSA :	25.78 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.79
Log Po/w (XLOGP3) :	1.81
Log Po/w (WLOGP) :	1.73
Log Po/w (MLOGP) :	1.16
Log Po/w (SILICOS-IT) :	2.67
Consensus Log Po/w :	1.83

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.03
Solubility :	0.226 mg/ml ; 0.000942 mol/l
Class :	Soluble
Log S (Ali) :	-1.97
Solubility :	2.57 mg/ml ; 0.0107 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.23
Solubility :	0.143 mg/ml ; 0.000596 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.0

Safety of [ 32779-38-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 32779-38-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 32779-38-7 ]
Downstream synthetic route of [ 32779-38-7 ]

[ 32779-38-7 ] Synthesis Path-Upstream 1~4

1
[ 1445-39-2 ]
[ 32779-38-7 ]

Yield	Reaction Conditions	Operation in experiment
31%	With tert.-butylnitrite; copper dichloride In acetonitrile at 20 - 60℃; Inert atmosphere	Step A. Preparation of 2-chloro-5-iodopyrimidine [00166] To a stirring solution of 5-iodopyrimidin-2-amine (2.21 g, 10.0 mmol) in CH₃CN (20 ml) at room temperature under argon was added copper (II) chloride (2.02 g, 15 mmol) and tert-butyi nitrite (1.55 g, 15 mmol). The reaction mixture was placed in a preheated oil bath (60 ⁰C) under Argon. The reaction mixture was cooled to room temperature and 20 ml of ether was added. The resulting insoluble material was filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM (~2 ml) and loaded onto an 80 g ISCO silica gel column which was eluted with a 20 min gradient from 0percent to 100percent EtOAc/Hexanes. 778 mg (31percent) of 2-chloro-5-iodopyrimidine was obtained as an off- white solid. ¹H NMR (400 MHz, CDCl₃) δ ppm 8.79 (s, 2 H).
28%	With sodium hydroxide; sodium nitrate In hydrogenchloride; water	(d) A suspension of 2-amino-5-iodopyrimidine (40 g) in concentrated hydrochloric acid (150 ml) was treated dropwise at a temperature of 25° to 30° C. with a solution of sodium nitrate (40 g) in water (70 ml). The reaction mixture was stirred at a temperature of 25° to 30° C. for a further 2 hr and then neutralised by the addition of aqueous 20percent sodium hydroxide, the temperature of the reaction mixture being maintained at 10° to 20° C. during the neutralisation by external cooling. The neutralised reaction mixture was filtered to remove solids and the solids were washed several times with chloroform. The filtrate was extracted with chloroform and the combined chloroform washings and extracts were dried and the chloroform was removed by distillation under reduced pressure to give crude 2-chloro-5-iodopyrimidine as a pale brown solid (12 g, 28percent) with m.p. 125° C. (Reference m.p. 129°-130° C. J. Chem. Soc. (C), 1971, 1889).
1.7 g	With tert.-butylnitrite; copper dichloride In acetonitrile at 70℃;	To a solution of 5-iodopyrimidin-2-amine (10.0 g, 0.045 mol) in acetonitrile (150 mL) was added CuCl₂ (11.57 g, 0.067 mol) and teri-butyl nitrite (6.99 g, 0.067 mol). The reaction mass was heated at 70°C for 5-6 h. The reaction mass was diluted with ether and the solid obtained was filtered off. The obtained product was purified with column chromatography on silica gel eluting with DCM to afford 1.700 g of the desired product

Reference： [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333
[2] Patent: WO2010/9183, 2010, A1, . Location in patent: Page/Page column 79
[3] Patent: US4248618, 1981, A,
[4] Patent: WO2013/186692, 2013, A1, . Location in patent: Page/Page column 62

2
[ 79387-69-2 ]
[ 32779-38-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 4, p. 1062 - 1074
[2] CrystEngComm, 2017, vol. 19, # 22, p. 3026 - 3036
[3] Organic Process Research and Development, 2007, vol. 11, # 2, p. 237 - 240

3
[ 32779-36-5 ]
[ 32779-38-7 ]

Reference： [1] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10480 - 10483

4
[ 124-41-4 ]
[ 32779-38-7 ]
[ 101803-06-9 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 4, p. 1062 - 1074

[ 32779-38-7 ] Synthesis Path-Downstream 1~58

1
[ 110-00-9 ]
[ 32779-38-7 ]
[ 63558-66-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1977,p. 621 - 624

2
[ 188290-36-0 ]
[ 32779-38-7 ]
[ 63558-67-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1977,p. 621 - 624

3
[ 188290-36-0 ]
[ 32779-38-7 ]
[ 63558-67-8 ]
2-chloro-5-thiophen-3-yl-pyrimidine [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1977,p. 621 - 624

4
[ 123-30-8 ]
[ 32779-38-7 ]
4-(5-Iodo-pyrimidin-2-yloxy)-phenylamine [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 2308 - 2315

5
[ 119-34-6 ]
[ 32779-38-7 ]
4-(5-Iodo-pyrimidin-2-yloxy)-3-nitro-phenylamine [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 2308 - 2315

6
[ 3964-52-1 ]
[ 32779-38-7 ]
[ 83173-31-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 2308 - 2315

7
[ 32779-38-7 ]
[ 75-08-1 ]
[ 104705-20-6 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1985,vol. 39,p. 691 - 696

9
[ 32779-38-7 ]
[ 192118-47-1 ]
2-(2-chloro-pyrimidin-5-yl)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1001 - 1004

10
[ 109230-57-1 ]
[ 32779-38-7 ]
[ 109230-58-2 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide;	EXAMPLE XV 2-(4-((5-Iodo-2-pyrimidinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide STR62 A mixture of 0.44 g (1.8 mmol) of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong>, 0.68 g (2 mmol) of 2-(4-hydroxyphenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide, 0.30 g (2.2 mmol) of powdered, anhydrous potassium carbonate and 25 ml of DMSO was warmed, under N2 at 100 C. for a period of two hours. The resulting mixture was poured into water and extracted with two portions of ether. The combined organic layers were washed with two portions of 5 percent aqueous NaOH, dried over MgSO4 and evaporated to dryness. The residue was recrystallized from methylcyclohexane to give 0.54 g (55 percent of theoretical) of the above-named product as colorless crystals, m.p. 106-107 C. (Compound 39)

Reference： [1]Patent: US5250690,1993,A

11
[ 1445-39-2 ]
[ 32779-38-7 ]

Yield	Reaction Conditions	Operation in experiment
31%	With tert.-butylnitrite; copper dichloride; In acetonitrile; at 20 - 60℃;Inert atmosphere;	Step A. Preparation of 2-chloro-5-iodopyrimidine [00166] To a stirring solution of <strong>[1445-39-2]5-iodopyrimidin-2-amine</strong> (2.21 g, 10.0 mmol) in CH3CN (20 ml) at room temperature under argon was added copper (II) chloride (2.02 g, 15 mmol) and tert-butyi nitrite (1.55 g, 15 mmol). The reaction mixture was placed in a preheated oil bath (60 0C) under Argon. The reaction mixture was cooled to room temperature and 20 ml of ether was added. The resulting insoluble material was filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM (~2 ml) and loaded onto an 80 g ISCO silica gel column which was eluted with a 20 min gradient from 0% to 100% EtOAc/Hexanes. 778 mg (31%) of 2-chloro-5-iodopyrimidine was obtained as an off- white solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.79 (s, 2 H).
28%	With sodium hydroxide; sodium nitrate; In hydrogenchloride; water;	(d) A suspension of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> (40 g) in concentrated hydrochloric acid (150 ml) was treated dropwise at a temperature of 25 to 30 C. with a solution of sodium nitrate (40 g) in water (70 ml). The reaction mixture was stirred at a temperature of 25 to 30 C. for a further 2 hr and then neutralised by the addition of aqueous 20% sodium hydroxide, the temperature of the reaction mixture being maintained at 10 to 20 C. during the neutralisation by external cooling. The neutralised reaction mixture was filtered to remove solids and the solids were washed several times with chloroform. The filtrate was extracted with chloroform and the combined chloroform washings and extracts were dried and the chloroform was removed by distillation under reduced pressure to give crude 2-chloro-5-iodopyrimidine as a pale brown solid (12 g, 28%) with m.p. 125 C. (Reference m.p. 129-130 C. J. Chem. Soc. (C), 1971, 1889).
1.7 g	With tert.-butylnitrite; copper dichloride; In acetonitrile; at 70℃;	To a solution of <strong>[1445-39-2]5-iodopyrimidin-2-amine</strong> (10.0 g, 0.045 mol) in acetonitrile (150 mL) was added CuCl2 (11.57 g, 0.067 mol) and teri-butyl nitrite (6.99 g, 0.067 mol). The reaction mass was heated at 70C for 5-6 h. The reaction mass was diluted with ether and the solid obtained was filtered off. The obtained product was purified with column chromatography on silica gel eluting with DCM to afford 1.700 g of the desired product

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333
[2]Patent: WO2010/9183,2010,A1 .Location in patent: Page/Page column 79
[3]Patent: US4248618,1981,A
[4]Patent: WO2013/186692,2013,A1 .Location in patent: Page/Page column 62

12
[ 110-85-0 ]
[ 32779-38-7 ]
[ 95847-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	EXAMPLE 66 Preparation of 1(5-iodo-2-pyrimidinyl)piperazine STR100 0.02 mol of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong>, 0.06 mol of piperazine and 100 ml of absolute dimethylformamide are heated to 100 for 45 minutes and then evaporated. The crystalline residue is shaken with potassium bicarbonate solution and methylene chloride. The substance contained in the methylene chloride phase is purified by column chromatography over silica gel 60. The amine obtained by elution with methylene chloride/methanol (7:3) is stirred with isopropyl ether and filtered off with suction.

Reference： [1]Patent: US4818756,1989,A

13
[ 773837-37-9 ]
[ 32779-38-7 ]
[ 1083329-46-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333

14
[ 32779-38-7 ]
[ 100-51-6 ]
[ 1083329-25-2 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333

15
[ 32779-38-7 ]
[ 100-51-6 ]
[ 1083329-27-4 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333

16
[ 54353-88-7 ]
[ 32779-38-7 ]
[ 1280223-25-7 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 1914 - 1917

17
[ 66399-30-2 ]
[ 32779-38-7 ]
C₁₂H₁₁FIN₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4832 - 4835

18
[ 1364767-30-5 ]
[ 32779-38-7 ]
[ 1364767-36-1 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; N-ethyl-N,N-diisopropylamine;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere;	To 1 .10 g (5.46 mmol) /V-ethyl-2-(4-ethynyl-phenyl)-propionamide (XVII.1 ) in 10 mL THF are added 1 .31 g (5.46 mmol) <strong>[32779-38-7]2-chloro-5-iodo-pyrimidine</strong> under argon, followed by 0.42 g (0.60 mmol) Pd(PPh3)2CI2 as catalyst, 57 mg (0.30 mmol) copper(l)iodide and 2.1 mL (12 mmol) DIPEA as base. The mixture is stirred at rt for 4 h. After that time, the mixture is filtered and the solvent is evaporated from the filtrate. The residue is purified by column chromatography (silicia gel; DCM:MeOH gradient 1 :0/1 : 1 ).Ci7Hi6CIN30 (M = 313.78 g/mol)ESI-MS: 314 [M+H]+ Rt (HPLC): 2.12 min (method L)
	With N-ethyl-N,N-diisopropylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere;	Example XVIIIExample XVIII.12-[4-(2-Chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamideTo 1.10 g (5.46 mmol) N-ethyl-2-(4-ethynyl-phenyl)-propionamide (XVII.1) in 10 mL THF are added 1.31 g (5.46 mmol) <strong>[32779-38-7]2-chloro-5-iodo-pyrimidine</strong> under argon, followed by 0.42 g (0.60 mmol) Pd(PPh3)2Cl2 as catalyst, 57 mg (0.30 mmol) copper(I)iodide and 2.1 mL (12 mmol) DIPEA as base. The mixture is stirred at rt for 4 h. After that time, the mixture is filtered and the solvent is evaporated from the filtrate. The residue is purified by column chromatography (silicia gel; DCM:MeOH gradient 1:0/1:1).C17H16ClN3O (M=313.78 g/mol)ESI-MS: 314 [M+H]+Rt (HPLC): 2.12 min (method L)

Reference： [1]Patent: WO2012/32014,2012,A1 .Location in patent: Page/Page column 92
[2]Patent: US2012/214782,2012,A1 .Location in patent: Page/Page column 39-40

19
[ 1353776-61-0 ]
[ 32779-38-7 ]
[ 1353777-14-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 130℃; for 2h;	Example XVIII.1 (S)-Cyclopropanecarboxylic acid (1-{4-[1-(5-iodo-pyrimidin-2-yl)-piperidin-4-yl]-phenyl}-ethyl)-amide 633 mg (2.5 mmol) <strong>[32779-38-7]2-Chloro-5-iodopyrimidine</strong>, 757 mg (2.5 mmol) (S)-cyclopropanecarboxylic acid [1-(4-piperidin-4-yl-phenyl)ethyl]-amide (V.4) and 0.855 mL (5.0 mmol) DIPEA in 10 mL NMP are stirred for 2 h at 130 C. After cooling to rt the mixture is treated with water and the precipitate is collected by filtration and triturated with ether to yield the desired compound. C21H25IN4O (M=476.4 g/mol); ESI-MS: 477 [M+H]+

Reference： [1]Patent: US2012/157425,2012,A1 .Location in patent: Page/Page column 58

20
[ 32779-38-7 ]
[ 1066-54-2 ]
[ 1383745-11-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; triethylamine; In tetrahydrofuran; at 50℃; for 12h;Inert atmosphere;	To a mixture of compound 1 (5 g, 20.80 mmol, 1 eq) and ethynyl(trimethyl)silane (4.09 g, 41.59 mmol, 5.76 mL, 2 eq) in THF (50 mL) was added CuI (118.82 mg, 623.88 umol, 0.03 eq) , Pd(PPh3)2Cl2 (437.90 mg, 623.88 umol, 0.03 eq) and Et3N (4.21 g, 41.59 mmol, 5.79 mL, 2 eq) under N2. The mixture was purged with N2 for three times and stirred at 50C for 12 hrs under N2. TLC showed it was finished (Petroleum ether: Ethyl acetate = 5: 1 Rf = 0.24). It was concentrated directly. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate = 8: 1, Petroleum ether: Ethyl acetate = 5: 1, Rf = 0.43) to give [00544] Compound 2 (2 g, 9.49 mmol, 45.64% yield) was obtained as a brown solid
	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 50℃;	A.3.3. Experimental procedure for the synthesis of alkyne SM-5c2-chloro-5-iodo-pyri m idi ne (51 3 mg , 2. 14 m mol) , Cu l ( 1 3.3 mg , 0.07 m mol) and (PPh3)2PdCI2 (40.7 mg, 0.06 mmol) are taken-up in dry THF (10 mL). NEt3 (0.57 mL, 4.05 mmol) and TMS-acetylene (0.42 mL, 2.91 mmol) are added and the mixture is stirred at 50 C overnight. The mixture is diluted with THF, filtered over celite and evaporated. The residue is taken-up in water and extracted 3 x with EtOAc. The combined organic layer is dried over MgS04, filtered and evaporated. The residual IM-3a (HPLC-MS: tRet. = 2.06 min; MS (M+H)+ = 21 1) is used without further purification. IM-3a (400 mg, 1.90 mmol) is taken-up in MeCN (6 mL). 1-(2-Methoxy-ethyl)-piperidin-4- yl-amine (474 mg, 2.99 mmol) and DI PEA (0.5 mL, 2.93 mmol) are added, the vial is sealed and heated to 60 C overnight until LC-MS indicates complete conversion. The reaction mixture containing SM-5c (HPLC-MS: tRet. = 1 .99 min; MS (M+H)+ = 333) is directly used in the next step (deprotection and cyloaddition reaction).
	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; at 50℃;	<strong>[32779-38-7]2-chloro-5-iodo-pyrimidine</strong> (513 mg, 2.14 mmol), CuI (13.3 mg, 0.07 mmol) and (PPh3)2PdCl2 (40.7 mg, 0.06 mmol) are taken-up in dry THF (10 mL). NEt3 (0.57 mL, 4.05 mmol) and TMS-acetylene (0.42 mL, 2.91 mmol) are added and the mixture is stirred at 50 C. overnight. The mixture is diluted with THF, filtered over Celite and evaporated. The residue is taken-up in water and extracted 3× with EtOAc. The combined organic layer is dried over MgSO4, filtered and evaporated. The residual IM-3a (HPLC-MS: tRet.=2.06 min; MS (M+H)+=211) is used without further purification.

Reference： [1]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 1062 - 1074
[2]Patent: WO2019/136442,2019,A1 .Location in patent: Paragraph 00543; 00544
[3]Patent: WO2012/85127,2012,A1 .Location in patent: Page/Page column 42-43
[4]Patent: US2012/322803,2012,A1 .Location in patent: Page/Page column 19-20

21
[ 33966-50-6 ]
[ 1363440-50-9 ]
[ 32779-38-7 ]
[ 1363436-28-5 ]

Yield	Reaction Conditions	Operation in experiment
	bis-triphenylphosphine-palladium(II) chloride; In water; at 20℃;	Example 15; N-(1-(4-((2-(sec-Butylamino)pyrimidin-5-yl)ethynyl)phenyl)propan-2-yl)acetamide; 2.50 g (12.4 mmol) N-(1-(4-ethynylphenyl)propan-2-yl)acetamide (I58.3), 3.0 g (12.42 mmol) <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> and 872 mg (1.24 mmol) bis(triphenylphosphine)dichloropalladium in 10 mL water and 10 mL sec-butylamine are stirred at r.t. over night. The reaction mixture is diluted with water and extracted with DCM. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, DCM/MeOH 98/2).C21H26N4O (M=350.5 g/mol)ESI-MS: 351 [M+H]+ Rt (HPLC): 2.07 (method E)

Reference： [1]Patent: US2012/214785,2012,A1 .Location in patent: Page/Page column 167

22
[ 766-98-3 ]
[ 32779-38-7 ]
[ 1404113-79-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere;	Step 1: 2-Chloro-5-(4-fluoro-phenylethynyl)-pyrimidine A solution of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (600 mg, 2.5 mmol), 1-ethynyl-4-fluorobenzene (330 mg, 2.75 mmol), triethylamine (556 mg, 761 mul, 5.49 mmol), and bis(triphenyl-phosphine)palladium (II) chloride (175 mg, 250 mumol) in 7 ml of THF was purged with argon. Then copper (I) iodide (23.8 mg, 125 mumol) was added and the reaction was heated for 2 h at room temperature. The dark solution was filtered and the solids were washed with THF. The residue was taken up in ethyl acetate, adsorbed onto 3 g of silicagel which was loaded onto a 50 g prepacked flash chromatography column. After elution with a 0% to 20% ethyl acetate in heptane gradient, the fractions containing the desired product were collected to yield 505 mg (87%) of the title compound as an crystalline light yellow solid, MS: m/e=233.1, 235.1 (M+H+).
87%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere;	Step 1 : 2-Chloro-5-(4-fluoro-phenylethynyl)-pyrimidine A solution of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (600 mg, 2.5 mmol), l-ethynyl-4-fiuorobenzene (330 mg, 2.75 mmol), triethylamine (556 mg, 761 mu, 5.49 mmol), and bis(triphenyl- phosphine)palladium (II) chloride (175 mg, 250 muiotaetaomicron) in 7 ml of THF was purged with argon. Then copper (I) iodide (23.8 mg, 125 muiotaetaomicron) was added and the reaction was heated for 2h at room temperature. The dark solution was filtered and the solids were washed with THF. The residue was taken up in ethyl acetate, adsorbed onto 3 g of silicagel which was loaded onto a 50 g prepacked flash chromatography column. After elution with a 0% to 20% ethyl acetate in heptane gradient, the fractions containing the desired product were collected to yield 505 mg (87%) of the title compound as an crystalline light yellow solid, MS: m/e = 233.1, 235.1 (M+H+).

Reference： [1]Patent: US2012/277213,2012,A1 .Location in patent: Page/Page column 22
[2]Patent: WO2012/146551,2012,A1 .Location in patent: Page/Page column 28-29

23
[ 32779-38-7 ]
pyridin-2-ylzinc(II) bromide [ No CAS ]
[ 374927-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 20℃; for 3h;Inert atmosphere;	Example A6. General experimental for the Negishi cross-couplingGeneral Scheme:Pd(PPh3)4 R99aZnBr + Ra 9a9Bb.l p99ap99b Representative Scheme:To a solution of tetrakis(triphenylphosphine)palladium (0.05 equiv) in THF was added the organozinc reagent (e.g., pyridin-2-ylzinc bromide, 2 equiv) at 15 C under N2. Then, a solution of aryl iodine (e.g., <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong>, 1 equiv) in THF was added. The reaction mixture was stirred at room temperature for 3 h. The mixture was poured into ¾0 and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2S04. After filtration and concentration, the crude product was purified by silica-gel column to give the C-C coupling product (e.g., 2-chloro-5- (pyridin-2-yl)pyrimidine).

Reference： [1]Patent: WO2012/170845,2012,A2 .Location in patent: Page/Page column 82-83

24
[ 81745-83-7 ]
[ 32779-38-7 ]
[ 374927-80-7 ]

Reference： [1]Organic Process Research and Development,2007,vol. 11,p. 237 - 240

25
[ 79387-69-2 ]
[ 32779-38-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 1062 - 1074
[2]CrystEngComm,2017,vol. 19,p. 3026 - 3036
[3]Organic Process Research and Development,2007,vol. 11,p. 237 - 240

26
[ 110-91-8 ]
[ 32779-38-7 ]
[ 866534-08-9 ]

Yield	Reaction Conditions	Operation in experiment
0.18 g	Reflux;	The mixture of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (0.200 g, 0.836 mmol) in morpholine (3.0 mL) was refluxed for 2-3 h. The reaction mass was quenched in water and the solid obtained was filtered off. The obtained solid was dried to afford 0.180 g of the desired product. 1H NMR (300 MHz, DMSO d6): delta 3.63(s, 8H), 8.52 (s, 2H); MS (m/z): 292.25 (M+H)+.

Reference： [1]Patent: WO2013/186692,2013,A1 .Location in patent: Page/Page column 62; 63

27
[ 1254058-34-8 ]
[ 32779-38-7 ]
[ 1453211-47-6 ]

Yield	Reaction Conditions	Operation in experiment
282 mg		Preparation Example 2 To a mixture of <strong>[1254058-34-8]3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline</strong> (253 mg) and isopropanol (6 mL), methanesulfonic acid (162 muL) was added followed by stirring at room temperature for 30 minutes. After that, 2-chloro-5-iodopyrimidine (200 mg) was added thereto, and the resulting mixture was stirred at 90 C. for 12 hours and further stirred at 130 C. for 2 hours under microwave irradiation. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution was added followed by extraction with chloroform. An organic layer obtained was dried over anhydrous sodium sulfate and then filtered. After the filtrate was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to give 5-iodo-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine (282 mg).

Reference： [1]Patent: US2014/142084,2014,A1 .Location in patent: Paragraph 0261

28
2-chloro-5-ethynylpyrimidine [ No CAS ]
[ 32779-38-7 ]
5,5'-ethyn-1,2-diyl-bis(2-chloropyrimidine) [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 1062 - 1074

29
[ 75-66-1 ]
[ 32779-38-7 ]
2-(t-butylthio)-5-iodopyrimidine [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 1062 - 1074

30
[ 124-41-4 ]
[ 32779-38-7 ]
[ 101803-06-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 1062 - 1074

31
[ 53279-93-9 ]
[ 32779-38-7 ]
2-(2-chloropyrimidin-5-yl)-4-phenylbutanenitrile [ No CAS ]
C₁₄H₁₂ClN₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 10480 - 10483

32
[ 32779-36-5 ]
[ 32779-38-7 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 10480 - 10483

33
[ 32779-38-7 ]
(N-heterocyclic carbene)Ag(SCF₂H) [ No CAS ]
C₅H₃ClF₂N₂S [ No CAS ]

Reference： [1]Chemical Science,2016,vol. 7,p. 3757 - 3762

34
[ 32779-38-7 ]
[ 57260-71-6 ]
[ 1027616-32-5 ]

Yield	Reaction Conditions	Operation in experiment
96.9%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 120℃; for 1h;Microwave irradiation;	A solution of <strong>[32779-38-7]2-chloro-5-iodo-pyrimidine</strong> (1.50 g, 6.24 mmol) , tert-butyl piperazine-1-carboxylate (1.39 g, 7.49 mmol) and DIPEA (1.62 g, 12.5 mmol) in i-PrOH (10 mL) is stirred at 120 for 1 hour in a microwave reactor. The mixture is diluted with EtOAc (100 mL) , washed with 1 N HCl acid, brine, dried over Na2SO4and concentrated to give the title compound (2.36 g, 6.05 mmol, 96.9) as a white solid, which is used without further purification. ES/MS m/z 335.0 (M-56) .

Reference： [1]Patent: WO2017/5069,2017,A1 .Location in patent: Page/Page column 12

35
2′,2′,2′-trichloroethyl α-diazoacetate [ No CAS ]
[ 32779-38-7 ]
2,2,2-trichloroethyl 2-(2-chloropyrimidin-5-yl)-2-diazoacetate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 3272 - 3275

36
[ 23357-46-2 ]
[ 32779-38-7 ]
5-iodo-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexylethylamine; In 1-methyl-pyrrolidin-2-one; at 160℃; for 1.5h;Microwave irradiation;	2.50 g (10.3 mmol) of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong>, 1.99 g (13.5 mmol) of (1R)-1,2,3,4-tetrahydronaphthalen-1-amine and 4.34 g (20.7 mmol) of dicyclohexylethylamine in 4.0 mL of 1-methyl-2-pyrrolidone are heated to 160 C. in a closed cuvette in the microwave for 90 minutes (Biotage Initiator, http://www.biotage.com/product-page/biotage-initiator). The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 4.00 g of 5-iodo-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]pyrimidin-2-amine (in waxy form) (98% yield at 90% purity).

Reference： [1]Patent: US2017/158644,2017,A1 .Location in patent: Paragraph 0280

37
[ 150058-63-2 ]
[ 32779-38-7 ]
tert-butyl[[6-(2-chloropyrimidin-5-yl)-2-pyridyl]methoxy]dimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		1.2 tert-butyl-[[6-(2-chloropyrimidin-5-yl)-2-pyridyl]methoxy]-dim A mixture of 0.6 g (2 mmol) (6-bromo-2-pyridyl)methoxy-tert-butyl-dimethyl-silane (vide supra) and THF is cooled to -70C and 0.9 ml 2.3 M solution of n-hexyl lithium in hexane (2.1 mmol) is added, followed by 2.0 ml 1 M solution of ZnCI2 in diethyl ether (2.0 mmol). The mixture is allowed to reach RT and stirred for 30 min. Then 0.1 g (0.1 mmol) Pd(PPh3) and 0.2 g (1 mmol) <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> in THF is added. The mixture is stirred at RT overnight, diluted with sat. NaHCO3-solution and extracted with EtOAc. The organic phases are pooled, dried and evaporated and the residue is purified by FC on aluminium oxide. Yield: 0.1 g (30%), ESI-MS: m/z = 336/338 (M+H)+, Rt(HPLC): 1.33 min (HPLC-A)

Reference： [1]Patent: WO2017/194453,2017,A1 .Location in patent: Page/Page column 43; 44

38
3-methoxyazetidine hydrochloride [ No CAS ]
[ 32779-38-7 ]
5-iodo-2-(3-methoxyazetidin-1-yl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.8 g	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 50℃;	IV.1 2-(3-methoxyazetidin-1-yl)-5-(4,4, 5, 5-tetramethyl-1,3, 2-dioxaborolan-2- yl)pyrimidine A mixture of 1.4 g (10.92 mmol) 3-methoxy-azetidine hydrochloride, 2.9 g (12.10 mmol) <strong>[32779-38-7]2-chloro-5-iodo-pyrimidine</strong>, 3.0 ml (17.61 mmol) DIPEA and ACN are heated to 50C overnight. The solvent is evaporated and the crude product purified by FC giving rise to 2.8 g 5-iodo-2-(3-methoxyazetidin-1 -yl)pyrimidine

Reference： [1]Patent: WO2017/194453,2017,A1 .Location in patent: Page/Page column 45

39
[ 26690-80-2 ]
[ 32779-38-7 ]
tert-butyl (2-((5-iodopyrimidin-2-yl)oxy)ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydroxide; In 1-methyl-pyrrolidin-2-one; at 100℃;	Step-a: Synthesis of tert-butyl (2-((5-iodopyrimidin-2-yl)oxy)ethyl)carbamate Into a 500-mL round-bottom flask was placed <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (10 g, 41.59 mmol, 1.00 equiv), NMP (200 mL), sodium hydroxide (3.3 g, 82.50 mmol, 2.00 equiv), and tert-butyl (2-hydroxyethyl)carbamate (6.7 g, 41.56 mmol, 1.00 equiv). The resulting solution was stirred at 100 C. until completion. The resulting solution was diluted with H2O (100 mL), extracted with of ethyl acetate (3*100 mL) and the organic layers combined, washed with brine (100 mL), dried over Na2SO4 and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:3) to deliver the title compound in 7.6 g (50%) as a brown solid.

Reference： [1]Patent: US2018/141913,2018,A1 .Location in patent: Paragraph 0433; 0434

40
(1S,3S)-3-(4-chlorophenyl)cyclobutan-1-ol [ No CAS ]
[ 32779-38-7 ]
2-[cis-3-(4-chlorophenyl)cyclobutyl]oxy}-5-iodopyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate; In tetrahydrofuran; at 40℃; for 3h;Inert atmosphere;	To a solution of cis-3- (4-chlorophenyl) cyclobutanol (2.297 g, 12.58 mmol) and <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (2.52 g, 10.48 mmol) in anhydrous THF (60 mL) was added sodium 2-methylpropan-2-olate (1.007 g, 10.48 mmol) . The resulting mixture was stirred at 40 C under N2for 3 h, then poured into water (50 mL) and extracted with EA (3 x 40 mL) . The combined organic layers were washed with brine (3 x 10 mL) , and dried over Na2SO4. After filtration and concentration, the resulting residue was purified by column chromatography (SiO2, PE: EA10: 1) to afford the title compound.1H NMR (400 MHz, CDCl3) 8.62 (s, 2H) , 7.27 (s, 2H) , 7.13-7.19 (m, 2H) , 5.14 (q, J7.43 Hz, 1H) , 3.04-3.19 (m, 1H) , 2.84-2.97 (m, 1H) , 2.19-2.36 (m, 1H) .

Reference： [1]Patent: WO2018/107415,2018,A1 .Location in patent: Page/Page column 89-90

41
[ 149771-44-8 ]
[ 32779-38-7 ]
tert-butyl 3-(5-iodopyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In 1-methyl-pyrrolidin-2-one; at 85℃;	General procedure: A solution of tert-butyl 3-oxa-7,9-diazabicyclo [3.3.1 jnonane-9-carboxylate(1 g, 4.38 mmol) 2-fluoro-5-iodopyridine (1.12 g, 5.04 mmol), and sodium carbonate (0.84 g,7.88 mmol) in 1-Methyl-2-pyrrolidinone (4 ml) was heated at 85 C overnight. The mixture wascooled to room temperature, diluted with water and extracted into DCM. The organic extract was dried over Na2SO4 filtered and concentrated under reduced pressure. The residue waspurified by silica chromatography to yield Sia (1.57 g, 62.3%). MS (ESI) mlz 431.9 [M+Hj . 1HNMR (400 MHz, Chloroform-d) oe 8.30 (dd, J = 2.4, 0.7 Hz, 1H), 7.66 (dd, J = 9.0, 2.3 Hz, 1H), 6.44 (d, J = 9.0 Hz, 1H), 4.25 (d, J = 12.7 Hz, 1H), 4.21 - 4.00 (m, 3H), 3.97 - 3.86 (m,2H), 3.80 (t, J= 11.9 Hz, 2H), 3.26 (t, J= 15.1 Hz, 2H), 1.48 (s, 9H).

Reference： [1]Patent: WO2018/145021,2018,A1 .Location in patent: Page/Page column 90; 91; 115

42
[ 75-31-0 ]
[ 32779-38-7 ]
5-iodo-N-isopropylpyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
815 mg	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 70℃; for 2h;	a) 5-iodo-N-isopropylpyrimidin-2-amine Propan-2-amine (0.713 mL) was added to a solution of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (1.0 g), DIPEA (1.49 mL) in DMSO (10 mL) at room temperature. The mixture was stirred at 70 C. for 2 hr. The reaction mixture was diluted with water at room temperature and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (815 mg). 1H NMR (300 MHz, DMSO-d6) delta 1.12 (6H, d, J=6.6 Hz), 3.94 (1H, dt, J=7.9, 6.6 Hz), 7.24 (1H, d, J=7.9 Hz), 8.39 (2H, s).

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 0989; 0990

43
[ 2854-16-2 ]
[ 32779-38-7 ]
1-((5-iodopyrimidin-2-yl)amino)-2-methylpropan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.13 g	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 70℃; for 16h;	a) 1-((5-iodopyrimidin-2-yl)amino)-2-methylpropan-2-ol 1-Amino-2-methylpropan-2-ol (0.39 mL) was added to a solution of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (1.0 g), DIPEA (1.49 mL) in DMSO (10 mL) at room temperature. The mixture was stirred at 70 C. for 16 hr. The reaction mixture was diluted with water at room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.13 g). 1H NMR (300 MHz, DMSO-d6) delta 1.08 (6H, s), 3.25 (2H, d, J=6.2 Hz), 4.48 (1H, s), 7.03 (1H, t, J=6.2 Hz), 8.39 (2H, s).

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 0997; 0998

44
[ 124-68-5 ]
[ 32779-38-7 ]
2-((5-iodopyrimidin-2-yl)amino)-2-methylpropan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
215 mg	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 70℃; for 16h;	a) 2-((5-iodopyrimidin-2-yl)amino)-2-methylpropan-1-ol DIPEA (1.49 mL) was added to a solution of 2-amino-2-methylpropan-1-ol (0.80 mL) and <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (1.0 g) in DMSO (10 mL) at room temperature. The mixture was stirred at 70 C. for 16 hr. The reaction mixture was diluted with water at room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (215 mg). 1H NMR (300 MHz, DMSO-d6) delta 1.27 (6H, s), 3.46 (2H, d, J=5.9 Hz), 4.84 (1H, t, J=5.9 Hz), 6.63 (1H, s), 8.40 (2H, s).

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 1001; 1002

45
[ 69843-13-6 ]
[ 32779-38-7 ]
5-iodo-N-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74 mg	With trifluoroacetic acid; In 2-methoxy-ethanol; at 100℃; for 16h;	a) 5-iodo-N-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine To a solution of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (100 mg) in 2-methoxyethanol (3 mL) were added 1-methyl-1H-pyrazol-4-amine (53 mg) and TFA (0.064 mL) at room temperature. The mixture was stirred at 100 C. for 16 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution at room temperature and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (74 mg). 1H NMR (300 MHz, DMSO-d6) delta 3.79 (3H, s), 7.44 (1H, s), 7.83 (1H, s), 8.55 (2H, s), 9.61 (1H, s).

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 1135; 1136

46
[ 2393-23-9 ]
[ 32779-38-7 ]
5-iodo-N-(4-methoxybenzyl)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.2 g	With triethylamine; In ethanol; at 120℃; for 0.166667h;Microwave irradiation;	a) 5-iodo-N-(4-methoxybenzyl)pyrimidin-2-amine 4-methoxybenzylamine (1.40 mL) was added to a solution of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (2.0 g) and triethylamine (1.75 mL) in ethanol (20 mL) at room temperature. The mixture was stirred under microwave irradiation at 120 C. for 10 min. The reaction mixture was subjected to water and the precipitate was collected by filtration to give the title compound (2.20 g). MS: [M+H]+ 341.9.

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 0890; 0891

47
5-chloro-N-(3-ethynyl-2,4-difluorophenyl)-2-methoxypyridine-3-sulfonamide [ No CAS ]
[ 32779-38-7 ]
5-chloro-N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)-2-methoxypyridine-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; for 1h;	a) 5-chloro-N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)-2-methoxypyridine-3-sulfonamide A mixture of 5-chloro-N-(3-ethynyl-2,4-difluorophenyl)-2-methoxypyridine-3-sulfonamide (359 mg), dichlorobis(tricyclohexylphosphine)palladium(II) (74 mg), DIPEA (2.62 mL), copper(I) iodide (38 mg), <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (313 mg) and DMSO (2.84 mL) was stirred at 60 C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give a crude purified product of the title compound (393 mg). The product was used without further purification for the next step. MS: [M+H]+ 471.0.

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 1172; 1173
[2]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1498 - 1503

48
2,5-dichloro-N-(3-ethynyl-2,4-difluorophenyl)benzenesulfonamide [ No CAS ]
[ 32779-38-7 ]
2,5-dichloro-N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
761 mg	With copper(l) iodide; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 10 - 35℃; for 16h;Inert atmosphere;	b) 2,5-dichloro-N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)benzenesulfonamide Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.56 g) was added to a solution of 2,5-dichloro-N-(3-ethynyl-2,4-difluorophenyl)benzenesulfonamide (3.0 g), <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (2.6 g), DIPEA (3.0 mL) and copper(I) iodide (79 mg) in THF (50 mL) at room temperature. The mixture was stirred under a nitrogen atmosphere at room temperature for 16 hr. The reaction mixture was filtered through celite, and the filtrate was diluted with water and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (761 mg). 1H NMR (300 MHz, DMSO-d6) delta 7.22-7.32 (1H, m), 7.42 (1H, td, J=8.9, 5.9 Hz), 7.71-7.81 (2H, m), 7.87 (1H, dd, J=2.0, 0.8 Hz), 9.03 (2H, s), 10.83 (1H, s).

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 0928; 0929

49
5-chloro-N-(3-ethynyl-2,4-difluorophenyl)-2-methylpyridine-3-sulfonamide [ No CAS ]
[ 32779-38-7 ]
5-chloro-N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)-2-methylpyridine-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
307 mg	With copper(l) iodide; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; for 1h;Microwave irradiation;	a) 5-chloro-N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)-2-methylpyridine-3-sulfonamide A mixture of <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (225 mg), 5-chloro-N-(3-ethynyl-2,4-difluorophenyl)-2-methylpyridine-3-sulfonamide (265 mg), dichlorobis(tricyclohexylphosphine)palladium(II) (58 mg), copper(I) iodide (30 mg), DIPEA (2.1 mL) and DMSO (2.1 mL) was stirred under microwave irradiation at 60 C. for 1 hr. The reaction mixture was diluted with ethyl acetate and water, and an insoluble material was removed by filtration. The filtrate was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (307 mg). 1H NMR (300 MHz, DMSO-d) delta 2.77 (3H, s), 7.23 (1H, td, J=8.9, 1.4 Hz), 7.41 (1H, td, J=9.0, 6.0 Hz), 8.06 (1H, d, J=2.2 Hz), 8.75 (1H, d, J=2.4 Hz), 9.02 (2H, s), 10.91 (1H, brs).

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 1236; 1237

50
5-chloro-3-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)-2-methoxybenzyl acetate [ No CAS ]
[ 32779-38-7 ]
5-chloro-3-(N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)sulfamoyl)-2-methoxybenzyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.37 g	With copper(l) iodide; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; for 1h;Microwave irradiation;	a) 5-chloro-3-(N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)sulfamoyl)-2-methoxybenzyl Acetate A mixture of 5-chloro-3-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)-2-methoxybenzyl acetate (3.00 g), dichlorobis(tricyclohexylphosphine)palladium(II) (515 mg), DIPEA (20 mL), copper(I) iodide (266 mg), <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (2.18 g) and DMSO (18 mL) was stirred under microwave irradiation at 60 C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give a residue. The obtained residue was washed with ethyl acetate/IPE to give the title compound (3.37 g). 1H NMR (300 MHz, DMSO-d6) delta 2.09 (3H, s), 3.82 (3H, s), 5.15 (2H, s), 7.19-7.30 (1H, m), 7.37 (1H, td, J=8.9, 6.0 Hz), 7.67 (1H, d, J=2.7 Hz), 7.78 (1H, d, J=2.7 Hz), 9.03 (2H, s), 10.43 (1H, s).

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 1086; 1087

51
5-chloro-7-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)-2,3-dihydrobenzofuran-3-yl acetate [ No CAS ]
[ 32779-38-7 ]
5-chloro-7-(N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)sulfamoyl)-2,3-dihydrobenzofuran-3-yl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.33 g	With copper(l) iodide; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; for 1h;Microwave irradiation;	a) 5-chloro-7-(N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)sulfamoyl)-2,3-dihydrobenzofuran-3-yl Acetate A mixture of 5-chloro-7-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)-2,3-dihydrobenzofuran-3-yl acetate (2.44 g), dichlorobis(tricyclohexylphosphine)palladium(II) (421 mg), DIPEA (16 mL), copper(I) iodide (217 mg), <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (1.65 g) and DMSO (16 mL) was stirred under microwave irradiation at 60 C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with water and ethyl acetate and an insoluble material was removed by filtration. The filtrate was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give a residue. The obtained residue was washed with ethyl acetate/IPE to give the title compound (2.33 g). 1H NMR (300 MHz, DMSO-d6) delta 2.03 (3H, s), 4.60-4.69 (1H, m), 4.71-4.81 (1H, m), 6.25 (1H, dd, J=6.4, 2.3 Hz), 7.21-7.31 (1H, m), 7.37 (1H, td, J=8.9, 6.0 Hz), 7.58 (1H, d, J=2.3 Hz), 7.80 (1H, d, J=2.1 Hz), 9.04 (2H, s), 10.56 (1H, s).

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 1222; 1223

52
5-chloro-N-(3-ethynyl-2,4-difluorophenyl)-2-(methylamino)pyridine-3-sulfonamide [ No CAS ]
[ 32779-38-7 ]
5-chloro-N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)-2-(methylamino)pyridine-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
256 mg	With copper(l) iodide; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; for 1h;	a) 5-chloro-N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)-2-(methylamino)pyridine-3-sulfonamide A mixture of 5-chloro-N-(3-ethynyl-2,4-difluorophenyl)-2-(methylamino)pyridine-3-sulfonamide (321 mg), dichlorobis(tricyclohexylphosphine)palladium(II) (66 mg), DIPEA (2.35 mL), copper(I) iodide (34 mg), <strong>[32779-38-7]2-chloro-5-iodopyrimidine</strong> (280 mg) and DMSO (2.55 mL) was stirred at 60 C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give a residue. The obtained residue was washed with ethyl acetate/IPE to give the title compound (256 mg). 1H NMR (300 MHz, DMSO-d6) delta 2.91 (3H, d, J=4.5 Hz), 6.62-6.70 (1H, m), 7.23-7.31 (1H, m), 7.41 (1H, td, J=8.9, 6.0 Hz), 7.72 (1H, d, J=2.6 Hz), 8.34 (1H, d, J=2.4 Hz), 9.03 (2H, s), 10.62 (1H, brs).

Reference： [1]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 1216; 1217

53
2,5-dichloro-3-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)benzyl acetate [ No CAS ]
[ 32779-38-7 ]
2,5-dichloro-3-(N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)sulfamoyl)benzyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.6 g	With copper(l) iodide; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; for 1h;Microwave irradiation;	f) 2,5-dichloro-3-(N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)sulfamoyl)benzyl acetate A mixture of 2,5-dichloro-3-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)benzyl acetate (1.45 g), dichlorobis(tricyclohexylphosphine)palladium(II) (246 mg), DIPEA (9 mL), copper(I) iodide (127 mg), 2-chloro-5-iodopyrimidin-2-amine (1.04 g) and DMSO (10 mL) was stirred under microwave irradiation at 60 C. for 1 hr. The same reaction was repeated twice in total, the reaction mixtures were combined, cooled to room temperature, diluted with water and ethyl acetate and an insoluble material was removed by filtration. The filtrate was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give a residue. The obtained residue was washed with ethyl acetate/IPE to give the title compound (2.60 g). 1H NMR (300 MHz, DMSO-d6) delta 2.12 (3H, s), 5.23 (2H, s), 7.21-7.31 (1H, m), 7.41 (1H, td, J=8.9, 5.9 Hz), 7.86-7.93 (2H, m), 9.03 (2H, s), 10.89 (1H, s).

Reference： [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1498 - 1503
[2]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 1188; 1189

54
1,3-dioxoisoindolin-2-yl tetrahydro-2H-pyran-4-carboxylate [ No CAS ]
[ 32779-38-7 ]
2-chloro-5-(tetrahydro-2H-pyran-4-yl)pyrimidine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2020,vol. 26,p. 186 - 191

55
[ 75-64-9 ]
[ 32779-38-7 ]
N-(tert-butyl)-5-iodopyrimidin-2-amine [ No CAS ]

Reference： [1]Chemical Communications,2020,vol. 56,p. 4284 - 4287

56
[ 1201935-87-6 ]
[ 32779-38-7 ]
2-(4-((5-iodopyrimidin-2-yl)amino)-3-methyl-1H-pyrazol-1-yl)ethyl-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In iso-butanol at 110℃; for 10h;	4 General procedure: Step 4: Add 2-chloro-5-iodopyrimidine (0.5g, 2mmol) and trifluoroacetic acid (20 microliters) to the colorless oil (0.3g) obtained in Step B1-3 in sec-butanol solution (10mL). Liter, catalytic) heating at 110 degrees Celsius for 10 hours, cooling, concentration, column chromatography purification to obtain a white solid product 0.6g, and then purified by preparative liquid chromatography to obtain the target intermediate B1 (N-(1,3-dimethyl- 1H-pyrazol-4-yl)-5-iodopyrimidin-2-amine, 250mg) and B2(N-(1,5-dimethyl-1H-pyrazol-4-yl)-5-iodopyrimidine- 2-amine, 120 mg).

Reference： [1]Current Patent Assignee: BEIJING SAITE MINGQIANG PHARMACEUTICAL TECH; BEIJING SCITECH MQ PHARMACEUTICALS - CN111484482, 2020, A Location in patent: Paragraph 0085; 0086; 0090-0093

57
[ 332069-74-6 ]
[ 32779-38-7 ]
5-iodo-N-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With trifluoroacetic acid In iso-butanol at 110℃; for 10h;	5 Step 5: 3-Methoxy-1-methyl-1H-pyrazole-4-amine (0.26g, 2mmol) in sec-butanol (2mL) was added with 2-chloro-5-iodopyrimidine (0.5g, 2.1mmol) and trifluoroacetic acid (20 microliters, catalytic) heated at 110 degrees Celsius for 10 hours, cooled, concentrated,Purified by column chromatography to obtain 0.55 g of 5-iodo-N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine as a white solid product with a yield of 83%.

Reference： [1]Current Patent Assignee: BEIJING SAITE MINGQIANG PHARMACEUTICAL TECH; BEIJING SCITECH MQ PHARMACEUTICALS - CN111484482, 2020, A Location in patent: Paragraph 0097; 0098; 0103

58
[ 32779-38-7 ]
trifluoro(vinyl)-λ4-borane potassium salt [ No CAS ]
[ 131467-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; caesium fluoride In 1,4-dioxane at 80℃; for 5h; Inert atmosphere;	2-chloro-5-vinylpyrimidine To a solution of 2-chloro-5-iodo-pyrimidine (2.0 g, 8.32 mmol) and potassium trifluorovinylborate (1.11 g, 8.32 mmol) in 1,4-dioxane (40 mL) at 15 °C were added CsF (2.53 g, 16.64 mmol) and Pd(dppf)Cl2 (609 mg, 0.83 mmol). The mixture was heated to 80 °C and stirred for 5 h. The mixture was diluted with H2O (60 mL) and extracted with EtOAc (3 × 20 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. LCMS: m/z = 141.1, 143.0 [M+H]+

Reference： [1]Current Patent Assignee: DENALI THERAPEUTICS INC - WO2022/109268, 2022, A1 Location in patent: Paragraph 0209; 0364

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P378
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H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 32779-38-7 ] {[proInfo.proName]}

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[ 32779-38-7 ] Synthesis Path-Upstream 1~4

[ 32779-38-7 ] Synthesis Path-Downstream 1~58

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Chlorides

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Pyrimidines

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