[ CAS No. 956034-07-4 ] {[proInfo.proName]}

Name: 956034-07-4|2,4-Dichlorofuro[3,2-d]pyrimidine|97%
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Quality Control of [ 956034-07-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 956034-07-4 ]

CAS No. :	956034-07-4	MDL No. :	MFCD11520866
Formula :	C₆H₂Cl₂N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OTFDNOQBJWBJJM-UHFFFAOYSA-N
M.W :	189.00	Pubchem ID :	45789968
Synonyms :

Calculated chemistry of [ 956034-07-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.82
TPSA :	38.92 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) :	-5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.14
Log Po/w (XLOGP3) :	2.62
Log Po/w (WLOGP) :	2.53
Log Po/w (MLOGP) :	0.97
Log Po/w (SILICOS-IT) :	2.72
Consensus Log Po/w :	2.2

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.27
Solubility :	0.102 mg/ml ; 0.00054 mol/l
Class :	Soluble
Log S (Ali) :	-3.09
Solubility :	0.155 mg/ml ; 0.000818 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.78
Solubility :	0.0317 mg/ml ; 0.000167 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.33

Safety of [ 956034-07-4 ]

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 [ 956034-07-4 ]

* 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 [ 956034-07-4 ]
Downstream synthetic route of [ 956034-07-4 ]

[ 956034-07-4 ] Synthesis Path-Upstream 1~5

1
[ 956034-06-3 ]
[ 956034-07-4 ]

Yield	Reaction Conditions	Operation in experiment
54%	at 130℃; for 3 h;	To furo[3,2-d]pyrimidine-2,4-diol (7J) (1.52 g, 10 mmol) was added dimethyl aniline (1 mL, 8 mmol), phosphorous oxychloride (0.9 mL, 9.65 mmol) and heated at 130 °C for 3h. The reaction mixture was cooled to room temperature and quenched carefully with ice. The solid obtained was collected by filtration washed with water and dried in vacuum to furnish 2,4- dichlorofuro[3,2-d]pyrimidine (7K) (1.02 g, 54percent) as a light brown solid; mp 107.3 °C; NMR (300 MHz, CDC13) δ 8.08 (d, J= 2.2, 1H), 7.02 (d, J = 2.2, 1H).
48%	at -40℃; for 48 h; Heating / reflux	Furo[3,2-d]pyrimidine-2,4-diol (39 mg, 1.0 eq) was dissolved in POCl₃ (1.8 ml). Mixture was cooled to -40° C. and N,N-diisopropylethylamine (0.45 ml) wad slowly added. Reaction mixture was then heated to reflux for 48 h, then cooled to room temperature Reaction mixture was poured into ice/water. Mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated aq. NaHCO₃, dried (Na₂SO₄) and concentrated to yield 2,4-dichlorofuro[3,2-d]pyrimidine (23 mg, 48percent) which was used in the next reaction without further purification.
48%	at -40℃; for 48 h; Heating / reflux	Furo[3,2-d]pyrimidine-2,4-diol 36 (39 mg, 1.0 eq) was dissolved in POCl₃(1.8 ml). Mixture was cooled to -40 °C and A^V-dusopropylethylamine (0.45 ml) wad slowly added. Reaction mixture was then heated to reflux for 48 h, then cooled to room temperature Reaction mixture was poured into ice/water. Mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated aq. NaHCO₃, dried (Na₂SO₄) and concentrated to yield 2,4-dichlorofuro[3,2-d]pyrimidine 37 (23 mg, 48percent) which was used in the next reaction without further purification.

48%	Stage #1: at -40℃; for 48 h; Heating / reflux Stage #2: at 20℃;	Furo[3,2-d]pyrimidine-2,4-diol 36 (39 mg, 1.0 eq) was dissolved in POCl₃(1.8 ml). Mixture was cooled to -40 ⁰C and iVJV-diisopropylethylamine (0.45 ml) wad slowly added. Reaction mixture was then heated to reflux for 48 h, then cooled to room temperature Reaction mixture was poured into ice/water. Mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated aq. NaHCO₃, dried (Na₂SO₄) and concentrated to yield 2,4-dichlorofuro[3,2-d]pyrimidine 37 (23 mg, 48percent) which was used in the next reaction without further purification.
41%	at -40℃; for 24 h; Reflux	At −40° C., to a solution of compound 30-d (0.86 g, 5.6 mmoL) in phosphorus oxychloride (8 mL) was added N,N-diisopropylethylamine (2 mL), after stirred for 10 minutes, the mixture was refluxed for 24 hours. After cooled to room temperature, the mixture was poured into ice water to quench the reaction, and then extracted with ethyl acetate (50 mL×3). The organic layers were combined, washed with water (20 mL×3) and saturated brine (20 mL) in sequence, then dried over anhydrous sodium sulfate, filtrated, the filtrate was concentrated under reduced pressure. The residue was purified by silica column chromatography (petroleum ether:ethyl acetate-100:1) to give white solid 30-c (430 mg, yield: 41percent). LC-MS (ESI): m/z=189 [M+H]⁺.

Reference： [1] Patent: WO2011/79230, 2011, A2, . Location in patent: Page/Page column 57
[2] Patent: US2008/76758, 2008, A1, . Location in patent: Page/Page column 78
[3] Patent: WO2008/70740, 2008, A1, . Location in patent: Page/Page column 138
[4] Patent: WO2008/73785, 2008, A2, . Location in patent: Page/Page column 165
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
[6] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0240; 0246

2
[ 956034-06-3 ]
[ 956034-07-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	at 130℃; for 2 h;	To a mixture of lH-furo[3,2-d]pyrimidine-2,4-dione (3.0 g, 0.020 mol) in NJf- dimethylaniline (2.0 mL, 0.016 mol) was added phosphorous oxychloride (18.0 mL, 0.193 mol) and the resulting mixture heated at 130 °C for 2 h. The resulting black solution was cooled to RT, then carefully quenched with crushed ice and H₂O, then extracted with EtOAc.The organic layer was isolated, dried (MgSO₄) and concentrated in vacuo to give the title compound as a tan solid (3.26 g, 87 percent). ¹H NMR (400 MHz, CDCl₃): δ 7.02 (d, J = 2.2 Hz, 1 H) and 8.08 (d, J = 2.2 Hz, 1 H).

Reference： [1] Patent: WO2008/152394, 2008, A1, . Location in patent: Page/Page column 25; 35
[2] MedChemComm, 2014, vol. 5, # 12, p. 1821 - 1828

3
[ 956034-03-0 ]
[ 956034-07-4 ]

Reference： [1] Patent: WO2011/79230, 2011, A2,
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
[3] Patent: US2015/336982, 2015, A1,
[4] Patent: WO2008/152394, 2008, A1,

4
[ 956034-04-1 ]
[ 956034-07-4 ]

Reference： [1] Patent: WO2011/79230, 2011, A2,
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
[3] Patent: US2015/336982, 2015, A1,
[4] Patent: WO2008/152394, 2008, A1,

5
[ 1093066-63-7 ]
[ 956034-07-4 ]

Reference： [1] Patent: WO2011/79230, 2011, A2,
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
[3] Patent: US2015/336982, 2015, A1,
[4] Patent: WO2008/152394, 2008, A1,

[ 956034-07-4 ] Synthesis Path-Downstream 1~14

1
[ 956034-04-1 ]
[ 956034-07-4 ]

Reference： [1]Patent: WO2011/79230,2011,A2
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 7815 - 7833
[3]Patent: US2015/336982,2015,A1
[4]Patent: WO2008/152394,2008,A1

2
[ 956034-07-4 ]
[ 1353552-97-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / methanol / 24 h / 20 °C 2: trifluoroacetic acid / iso-butanol / 12 h / 100 °C 3: hydrogenchloride; iron / ethanol; water / 1 h / 100 °C 4: sodium hydrogencarbonate / water; tetrahydrofuran / 0.5 h / 0 °C

Reference： [1]Current Patent Assignee: HANMI SCIENCE CO LTD - WO2011/162515, 2011, A2

3
[ 956034-07-4 ]
[ 336191-17-4 ]
[ 1372534-58-1 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine; In 1,4-dioxane; at 25℃; for 12h;	Step A: teri-Butyl 8-(2-chlorofuro[3,2-i/]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2- carboxylateA mixture of teri-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (0.83 g, 3.4 mmol, Alfa Aesar), 2,4-dichlorofuro[3,2-i/]pyrimidine (0.65 g, 3.4 mmol, ArkPharm) and TEA (0.96 mL, 6.9 mmol) in 1,4-dioxane (35 mL) was stirred at about 25 C for about 12 h. Water (4 mL) and EtOAc (25 mL) were added and the layers were separated. The organic layer was concentrated under reduced pressure to give teri-butyl 8-(2-chlorofuro[3,2-i/]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2- carboxylate (1.25 g, 55%): LC/MS (Table 2, Method f) Rt = 2.12 min; MS m/z: 393 (M+H)+.

Reference： [1]Patent: WO2012/48222,2012,A1 .Location in patent: Page/Page column 211

4
[ 956034-07-4 ]
[ 2919-23-5 ]
[ 1372534-30-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydride; In 1,4-dioxane; mineral oil; at 20℃;	General Procedure Y: Nucleophilic displacement of an aryl halide with an alcoholTo a solution of an aryl halide and an appropriate organic solvent (such as 1 ,4-dioxane, DME, n- butanol, THF or DMF, preferably 1,4-dioxane) is added an alcohol (1 to 10 equiv, preferably 1 to 5 equiv) and a base (such as NaH, TEA, DIEA, K2C03, preferably NaH; 1 to 5 equiv, preferably 1 to 1.5 equiv). The resulting mixture is stirred at about 0 to 150 C (preferably about 20 to 80 C) for a period of about 1 h to 24 h (preferably about 4 to 16). The mixture may optionally be concentrated in vacuo to give the target compound. Alternatively, the mixture is optionally filtered through a media (such as silica gel or Celite) which is rinsed with an appropriate solvent (such as EtOAc, 1,4-dioxane, THF, MeCN, DCM, Et20, MeOH, EtOH) and then optionally concentrated in vacuo to give a residue as the target compound. Either the residue or the solution may be optionally partitioned between water and an organic solvent (such as EtOAc, Et20 or DCM). The organic layer is isolated and may optionally be washed in no particular order with water and/or aqueous solutions containing an acid (such as HC1, AcOH or NH4C1) and/or aqueous solutions containing a base (such as NaHC03, Na2C03, NaOH, KOH or NH4OH) and/or aqueous solutions containing an inorganic salt (such as NaCl Na2S03 or Na2S203). The organic solution may then be optionally dried with a drying agent (such as anhydrous MgS04 or Na2S04), filtered and concentrated in vacuo to give the target compound.Illustration of General Procedure YPreparation No.Y.l -Chloro-4-cyclobutoxyfuro[3,2-</]pyrimidineTo a flask was added <strong>[2919-23-5]cyclobutanol</strong> (0.820 mL, 10.5 mmol), 2-chloro-4-cyclobutoxyfuro[3,2- i/]pyrimidine (0.400 g, 2.11 mmol, ArkPharm) and 1,4-dioxane (0.1 mL). To the mixture was added NaH (60% dispersion in mineral oil, 0.102 g, 2.54 mmol). The mixture was stirred at rt overnight. The mixture was extracted with DCM (3 x 5 mL) and water (5 mL). The organic layer was dried over Mg2S04, filtered and concentrated under reduced pressure. Water (20 mL) was added to the residue and the precipitate was collected by filtration and dried in vacuum oven at about 60 C overnight to give 2-chloro-4-cyclobutoxyfuro[3,2-J]pyrimidine (0.4g, 91 %): LC/MS (Table 2, Method c) R, = 2.57 min.; MS m/z: 225 (M+H)+.

Reference： [1]Patent: WO2012/48222,2012,A1 .Location in patent: Page/Page column 186-187

5
[ 956034-07-4 ]
[ 1153949-15-5 ]
C₁₉H₁₉ClN₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere;	30 Preparation of Compound 30-b Under nitrogen, to a suspension of compound 5-a (640 mg, 1.65 mmol), compound 30-c (280 mg, 1.49 mmol) and potassium carbonate (720 mg, 5.2 mmol) in 1,4-dioxane (2 mL) and water (6 mL) was added Pd(PPh3)4 (57 mg, 0.05 mmol), the mixture was heated to 80° C. and stirred for 16 hours. The mixture was then concentrated under reduced pressure, the residue was diluted with water (20 mL), extracted with dichloromethane (20 mL×3). The organic layer were combined, washed with water (10 mL×3) and saturated brine (10 mL) in sequence, then dried over anhydrous sodium sulfate, filtrated, the filtrate was concentrated under reduced pressure. The residue was purified by silica column chromatography (petroleum ether:ethyl acetate=3:1) to give light yellow solid 30-b (620 mg, yield: 70%). LC-MS (ESI): nm/z=415 [M+H]+.

Reference： [1]Current Patent Assignee: GUANGZHOU MAXINOVEL PHARMACEUTICALS - US2015/336982, 2015, A1 Location in patent: Paragraph 0240; 0247

6
[ 956034-07-4 ]
[ 1083326-75-3 ]
C₁₃H₁₁ClN₄O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere;	To a reaction flask were added compound 27-c (36 mg, 0.106 mmol), compound 38-b (prepared according to the method disclosed in: WO 2011/079230 A2) (20 mg, 0.106 mmol), PdC12(dppf) (4 mg, 0.005 mmol), 2 N sodium carbonate aqueous solution (0.16 mE, 0.32 mmol, 3.0 equiv.) and 1 ,4-dioxane (1 mE). The mixture was stirred under nitrogen atmosphere at 80 C. overnight. The reaction mixture was concentrated under reduced pressure, and then partitioned between water (15 mE) and dichioromethane (20 mE). The organic phase was separated out, dried over anhydrous sodium sulfate, and concentrated under reduced pressure, to obtain compound 38-a (40 mg). EC-MS (ESI): mlz=354.7 (M+H).

Reference： [1]Patent: US2016/214994,2016,A1 .Location in patent: Paragraph 0225; 0226

7
[ 858131-73-4 ]
[ 956034-07-4 ]
[ 98-80-6 ]
C₃₆H₂₃N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 13h; Inert atmosphere; Reflux;	Step2: synthesis of compound (A-5) General procedure: Intermediate product A 20.0 g (50.5 mmol), 4 - phenylboronic Acid 7.39 g (60.6 mmol) and K2CO3 16.8 g (121 mmol), Pd (PPh3) 4 2.92 g (2.53 mmmol) and THF 400 ml, distilled water 200 It was suspended in a stream of nitrogen mlReflux for 13 hours and stirred. After the reaction was cooled and the precipitated solid was filtered. Methanol and the solid several times with water and dried after ssikeun dichloromethane (methylene chloride: MC) and hexane (n-hexane: n-Hex) by recrystallization to obtain a compound (A-5) 18.4g (yield: 83%) was obtained .To the specific compounds according to the embodiment of thepresent invention prepared according to the synthetic methods as describedabove it is shown in Table 1 below.

Reference： [1]Current Patent Assignee: SAMSUNG C&T CORPORATION - KR101648141, 2016, B1 Location in patent: Paragraph 0176; 0192; 0193

8
[ 956034-07-4 ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chlorofuro[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃; for 5.0h;	[0111] A mixture of 2,4-dichlorofuro[3,2-d]pyrimidine (150 mg, 0.79 mmol), 4-(lH- pyrazol-4-yl)aniline (126.3 mg, 0.79 mmol), and diisopropylethylamine (0.28 mL, 1.59 mmol) in DMF (1.59 mL) was heated at 100 C for 5 h. TLC showed the reaction was complete. The mixture was then diluted with water. The resulted yellow precipitate was filtered and washed with water and dried in vacuo to provide 210 mg (85%) title compound which was used directly for next step reaction without further purification.

Reference： [1]Patent: WO2016/210330,2016,A1 .Location in patent: Paragraph 0110-0111

9
[ 956034-07-4 ]
[ 325775-44-8 ]
tert-butyl 3-(((2-chloro-furo[3,2-d]pyrimidin-4-yl)amino)methyl)azetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.5%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;Reflux;	Step 1: preparation of tert-butyl 3-(((2-chloro-furo[3,2-d]pyrimidin-4-yl)amino) methyl)azetidine-1-carboxylate (0257) (0258) 2,4-Dichloro-furo[3,2-d]pyrimidine (189 mg, 1 mmol) and <strong>[325775-44-8]tert-butyl 3-(aminomethyl)azetidine-1-carboxylate</strong> (186 mg, 1 mmol) were dissolved in tetrahydrofuran (20 mL), followed by the addition of N,N-diisopropylethylamine (258 mg, 2 mmol). The reaction solution was reacted under reflux overnight, then cooled to room temperature, and concentrated. The residue was added with water (20 mL), and extracted with ethyl acetate (10 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: n-hexane: ethyl acetate = 6 : 1), to give a white solid (283 mg). Yield: 83.5%. MS (ESI, m/z): [M+H]+: 339.1.

Reference： [1]Patent: EP3048105,2016,A1 .Location in patent: Paragraph 0257; 0258

10
[ 956034-07-4 ]
[ 1228947-14-5 ]
N-(3-methylisothiazol-5 yl)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)furo[3,2-d]pyrimidin-2-amine [ No CAS ]

Reference： [1]Patent: WO2017/205766,2017,A1

11
[ 956034-07-4 ]
[ 1228947-14-5 ]
2-chloro-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)furo[3,2-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		A mixture of(lr,4r)-4-morpholinocyclohexan-1-ol (0.53 g, 2.9 mmol, 1.1 eq) in 5.0 mL of THF was prepared and 60% NaH (0.56 g, 14 mmol, 5.3 eq) was added. The reaction mixture was stirred at room temperature for 30 mm and 2,4-dichlorofuro[3,2-djpyrimidine (0.50 g, 2.6 mmol, 1.0 eq) was added and the resulting mixture was heated at 60 C for 3 hr. The reaction was cooled to room temperature and quenched with saturated aqueous ammonium chloride. The quenched mixture was rotary evaporated and purified on normal phase Combi-Flash using a 40 g column and eluting with a gradient of 0-20% MeOH/CH2C12 in 10 mm. The product containing fractions were combined and rotary evaporated to give 2-chloro-4-(((lr,4r)-4- morpholinocyclohexyl)oxy)furo[3,2-djpyrimidine (0.59 g, 1.7 mmol, 60% yield) as a white solid. LC-MS:M+H=338.0

Reference： [1]Patent: WO2017/205766,2017,A1 .Location in patent: Paragraph 00447

12
[ 956034-07-4 ]
[ 89088-69-7 ]
2-chloro-N-(1-methyl-1H-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; for 24h;Reflux;	To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), <strong>[89088-69-7]1-methyl-1H-imidazol-4-amine hydrochloride</strong> (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).
59%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; for 24h;Reflux;	To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), <strong>[89088-69-7]1-methyl-1H-imidazol-4-amine hydrochloride</strong> (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

Reference： [1]Patent: WO2018/232094,2018,A1 .Location in patent: Page/Page column 89
[2]Patent: WO2018/232094,2018,A1 .Location in patent: Page/Page column 89; 167

13
[ 956034-07-4 ]
[ 1890954-24-1 ]
[ 2313366-52-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 2,4-dichloro-furo[3,2-d]pyrimidine With lithium diisopropyl amide In tetrahydrofuran at -60℃; for 1h; Stage #2: 2,6-difluoro-3,5-dimethoxybenzene(meth)aldehyde In tetrahydrofuran at -60℃; for 2h;

Reference： [1]Current Patent Assignee: ADVENT PHARMA; ADVNET PHARMA - WO2019/80878, 2019, A1 Location in patent: Page/Page column 62; 63

14
[ 832114-05-3 ]
[ 956034-07-4 ]
tert-butyl 3-(2-chlorofuro[3,2-d]pyrimidin-4-yl)benzylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine In 1,4-dioxane; water at 120℃; for 1.5h; Inert atmosphere;	1 Step-l : Preparation of /ert-butyl 3-(2-chlorofuro[3,2-d]pyrimidin-4-yl)benzylcarbamate (36b) Compound 36b was prepared according to the procedure reported in step-3 of Scheme- 1 from 2,4-dichlorofuro[3,2-d]pyrimidine (36a) (3 g, 15.87 mmol; CASNo. 956034-07-4) in dioxane (100 mL) using /er/-butyl 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzylcarbamate (3b) (3.78 g, 11.34 mmol), tripotassium phosphate (8.31 mL, 24.94 mmol, 3 M aqueous solution) in water (1 mL), tricyclohexylphosphine (0.95 g, 3.38 mmol) and Pd2(dba)3 (1.04 g, 1.13 mmol) in argon atmosphere and heating in an oil bath at 120 °C for 1.5 h. This gave after workup and purification by flash column chromatography [silica (40 g), eluting with EtOAc in hexane from 0-70%] /er/-butyl 3-(2-chlorofuro[3,2-d]pyrimidin-4- yl)benzylcarbamate (36b) (2.65 g, 65 % yield) as a white solid; NMR (300 MHz, DMSO- de) d 8.74 (d, J = 2.3 Hz, 1H), 8.29 (d, J = 7.5 Hz, 2H), 7.66 - 7.47 (m, 3H), 7.33 (d, J = 2.3 Hz, 1H), 4.26 (d, J = 6.2 Hz, 2H), 1.42 (s, 9H); MS (ES-): 358.3 & 360.3 (M-l).

Reference： [1]Current Patent Assignee: BIOCRYST PHARM INC; BIOCRYST PHARMACEUTICALS INC - WO2019/195720, 2019, A1 Location in patent: Page/Page column 166

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[ CAS No. 956034-07-4 ] {[proInfo.proName]}

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[ 956034-07-4 ] Synthesis Path-Upstream 1~5

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Chlorides

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Other Aromatic Heterocycles

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[ 956034-07-4 ]

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[ 956034-07-4 ]