[ CAS No. 2927-71-1 ] {[proInfo.proName]}

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Quality Control of [ 2927-71-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2927-71-1 ]

SDS Specification

Alternatived Products of [ 2927-71-1 ]

Product Details of [ 2927-71-1 ]

CAS No. :	2927-71-1	MDL No. :	MFCD00233551
Formula :	C₄HCl₂FN₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	WHPFEQUEHBULBW-UHFFFAOYSA-N
M.W :	166.97	Pubchem ID :	250705
Synonyms :

Calculated chemistry of [ 2927-71-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.01
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) :	-5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.74
Log Po/w (XLOGP3) :	2.23
Log Po/w (WLOGP) :	2.34
Log Po/w (MLOGP) :	1.25
Log Po/w (SILICOS-IT) :	2.77
Consensus Log Po/w :	2.07

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.77
Solubility :	0.281 mg/ml ; 0.00168 mol/l
Class :	Soluble
Log S (Ali) :	-2.41
Solubility :	0.655 mg/ml ; 0.00392 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.16
Solubility :	0.117 mg/ml ; 0.000698 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.7

Safety of [ 2927-71-1 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H302-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2927-71-1 ]

* 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.

Downstream synthetic route of [ 2927-71-1 ]

[ 2927-71-1 ] Synthesis Path-Downstream 1~8

1
[ 398491-61-7 ]
[ 2927-71-1 ]
[ 1046788-00-4 ]

Yield	Reaction Conditions	Operation in experiment
50%		Intermediate BKiQ: tert-butyl 3-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1 H)-carboxylate.; To a solution of BKi) (8.01 g, 31.7 mmol) and 2,4-dichloro-5-fluoro pyrimidine (5.30 g,31.7 mmol) in DMSO (40 mL) was added potassium dihygrogenphosphate (4.32 g, 31.7 mmol) followed by H3PO4 (0.62 g, 6.4 mmol). The reaction was placed in a 95 0C oil bath and heated for 2Oh. The crude reaction was cooled to room temperature then poured into ice cold NaHCO3 (sat, 100 mL) followed by addition of EtOAC (75 mL). The resulting mixture was filtered to give the desired compound BKN) as a white solid (6.1 g,50%). 1H NMR (300 MHz, DMSO-J6) delta ppm 1.35- 1.50 (m, 9 H), 1.56- 1.65 (m, 6 H),4.37- 4.64 (m, 2 H), 8.09- 8.42 (m, 1 H), 10.70 (br. s., 1 H), 12.53 (br. s., 1 H). Mass spectrum: Calcd for C16H2ICIFN6O2 (M+H): 383. Found 383.

Reference： [1]Patent: WO2008/96260,2008,A1 .Location in patent: Page/Page column 43-44

2
[ 4138-26-5 ]
[ 2927-71-1 ]
[ 1192711-54-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 20h;Product distribution / selectivity;	A mixture of 2,4-dichloro-5-fluoropyrimidine (167 mg, 1.00 mmol), <strong>[4138-26-5]nipecotamide</strong> (128 mg, 1.00 mmol) and DIEA (0.350 mL, 2.01 mmol) in CH3CN (4 mL) was stirred at room temperature for 20 h. It was concentrated in vacuo. The residue was dissolved in nBuOH (4 mL). 2 mL of the nBuOH solution was taken, to which 6-aminoindazole (100 mg, 0.75 mmol) was added. The solution was stirred at 116 0C for 6 h. nBuOH was removed in vacuo. The residue was purified by HPLC to give the titled compound (63 mg). MS 356.3 (M+H); UV 206.8, 249.8, 276.8, 291.8 nm.

Reference： [1]Patent: WO2009/131687,2009,A2 .Location in patent: Page/Page column 114

3
[ 149423-70-1 ]
[ 2927-71-1 ]
[ 1192712-34-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20.0℃; for 20.0h;	To a mixture of 2,4-dichloro-5-fluoropyrimidine (226 mg, 1.35 mmol) and benzyl (ls,4s)-4-aminocyclohexylcarbamate (335 mg, 1.35 mmol) in CH3CN (6 mL), DIEA (0.600 mL, 3.45 mmol) was added. The mixture was stirred at room temperature for 20 h. Water and EtOAc were added. The organic phase was separated, washed with IN HCl, dried over Na2SO4, concentrated in vacuo to give benzyl (ls,4s)-4-(2-chloro-5-fluoropyrimidin-4- ylamino)cyclohexylcarbamate (511 mg).

Reference： [1]Patent: WO2009/131687,2009,A2 .Location in patent: Page/Page column 189

4
[ 67-56-1 ]
[ 2927-71-1 ]
[ 37554-70-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium; at 20℃;	Sodium (0.45 g, 19.6 mmol) was added in portions to methanol (20 mL). Once all the sodium had reacted, a solution of 2,4-dichloro-5-fluoropyrimidine (Preparation 15a, 3.25 g, 19.5 mmol) in methanol (10 mL) was added and the mixture was stirred at ambient temperature overnight. The mixture was diluted with water and extracted with diethyl ether. The organic layer was washed with water, brine, dried (MgS04), filtered and the solvent was removed under reduced pressure to give the title compound (81%) as an orange solid, which was used without further purification.LRMS (m/z): 163 (M+1)+.H-NMR 5 (CDCI3): 4.11 (s, 3H), 8.20 (d, 1 H)
81%		title compound (81%) as an orange solid, which was used without further purification.LRMS (m/z): 163 (M+1)+.1H-NMR delta (CDCl3): 4.11 (s, 3H), 8.20 (d, 1 H)
80%	With sodium; at 20℃;	To a mixture of sodium (450 mg, 19 mmol) in methanol (20 mL) was added a solution of 2,4-dichloro-5-fluoropyrimidine (3.25 g, 19 mmol) in methanol (10ml_). The reaction mixture was stirred at room temperature overnight before being partitioned between water and diethyl ether. The organic phase was separated, washed with brine and evaporated to dryness to give the title compound as an orange oil (80%), which was used in the next step without further purification.1H-NMR delta (400 MHz, CDCI3): 4.1 (s, 3H), 8.2 (s, 1 H).

80%

With sodium; at 20℃;

sodium (450 mg, 19 mmol) in methanol (20 mL) was added a solution of 2,4-dichloro-5-fluoropyrimidine (3.25 g, 19 mmol) in methanol (10mL). The reaction mixture was stirred at room temperature overnight before being partitioned between water and diethyl ether. The organic phase was separated, washed with brine and evaporated to dryness to give the title compound as an orange oil (80%), which was used in the next step without further purification.1H-NMR delta (400 MHz, CDCl3): 4.11 (s, 3H), 8.20 (s, 1 H).

Reference： [1]Patent: WO2011/76419,2011,A1 .Location in patent: Page/Page column 112
[2]Patent: EP2338888,2011,A1 .Location in patent: Paragraph 0144; 0146
[3]Patent: WO2011/101161,2011,A1 .Location in patent: Page/Page column 93
[4]Patent: EP2360158,2011,A1 .Location in patent: Paragraph 0150
[5]Journal of Medicinal Chemistry,2018,vol. 61,p. 10700 - 10708

5
IPr₂NEt [ No CAS ]
[ 2927-71-1 ]
[ 162167-97-7 ]
(R)-tert-butyl 3-((2-chloro-5-fluoropyrimidin-4-ylamino)methyl)-piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Formation of (R)-tert-butyl 3-((2-chloro-5-fluoropyrimidin-4-ylamino)methyl)-piperidine-1-carboxylate (11a)To a solution of 2,4-dichloro-5-fluoropyrimidine (0.43 g, 2.59 mmol) and (R)-<strong>[162167-97-7]tert-butyl 3-(aminomethyl)piperidine-1-carboxylate</strong> (0.56 g, 2.59 mmol) in THF (50 mL) was added iPr2NEt (0.45 mL, 2.59 mmol).The reaction mixture was heated at 80° C. at for 8 h.The solvent was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography (5-30percent EtOAc/hexanes) to afford the desired product, 11a.

Reference： [1]Patent: US2012/171245,2012,A1

6
[ 85290-78-4 ]
[ 2927-71-1 ]
[ 1307803-02-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In acetonitrile; at 20 - 80℃;	solution of ethyl 3-methyl- f/-pyrazole-4-carboxylate 2 (3.15 g, 20.5 mmol) in anhydrous acetonitrile were added potassium carbonate (5.7 g, 41 mmol) and 2,4-dichloro-5-fluoropyrimidine 1 at room temperature. The resulting suspension was heated at 80 C for 3 hours with monitoring a reaction with LC-MS P T/US2010/056583- 43 - or thin layer chromatography (TLC). It was diluted with ethyl acetate and washedwith brine. The collected organic layer was dried over anhydrous sodium sulfateand then partially concentrated in vacou. To this, n-hexanes were added to formpale yellow precipitates. The resulting solids were collected by filtration and rinsed with n-hexanes and then dried with high vacuum to give 4.9 g (85 %) of the targetintermediate 1; MS (ESI) m/z 285 [M+H]+.
85%	With potassium carbonate; In acetonitrile; at 80℃; for 3h;	To a solution of ethyl 3-methyl-iH-pyrrole-4-carboxylate (3.15 g, 20.5 mmol) in acetonitrile (MeCN) were added potassium carbonate (5.7 g, 41 mmol) and 2,4- dichloro-5-fluoropyrimidine (3.4 g, 20.5 mmol) at room temperature. The resulting slurry was heated at 80 C for 3 hours with monitoring a reaction with LC-MS or thin layer chromatography (TLC). It was diluted with ethyl acetate and washed with brine The collected organic layer was dried over anhydrous sodium sulfate and then partially concentrated in vacuo. To this, w-hexanes were added to form pale yellow precipitates. The resulting solids were collected by filtration and rinsed with n- hexanes and then dried under high vacuum to give 4.9 g (85 %) of the target intermediate 3; MS (ESI) m/z 285 [M+H]+.

Reference： [1]Patent: WO2011/60295,2011,A1 .Location in patent: Page/Page column 42-43
[2]Patent: WO2013/109882,2013,A1 .Location in patent: Page/Page column 55; 56

7
[ 5900-59-4 ]
[ 2927-71-1 ]
C₁₁H₇Cl₂FN₄O [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 93,p. 523 - 538

8
[ 1197953-47-1 ]
[ 2927-71-1 ]
(2-((2-chloro-5-fluoropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃;	To a solution of 2,4-dichloro-5-fluoropyrimidine (0.5 g, 2.99 mmol) and (2-aminophenyl)dimethylphosphineoxide (0.323 g, 1.907 mmol) in DMF (6.36 mL) wasadded potassium carbonate (0.828 g, 5.99 mmol). The reactionmixture was stirred at 70 °C for overnight. After completion of thereaction, the resulting mixture was cooled to room temperature,quenched with water, extracted with DCM and washed with brine.The combined organic layer was dried over Na2SO4, filtered andconcentrated under reduced pressure. The residue was purified byflash column chromatography on silica gel (0-20percent MeOH in DCM)to give 3f as a yellowish solid (0.178 g, 31percent). 1H NMR (400 MHz,DMSO-d6) delta 12.09 (s, 1H), 8.54-8.51 (m, 1H), 8.37 (br d, J = 3.0 Hz,1H), 7.68-7.60 (m, 2H), 7.23 (br t, J = 6.7 Hz, 1H),1.83 (s, 3H),1.80 (s,3H); LC/MS (ESI) m/z 300.00 [M+H]+.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 136,p. 497 - 510

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Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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Ghs Precautionary Statements

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Code	Phrase
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P222	Do not allow contact with air.
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P230	Keep wetted
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P262	Do not get in eyes, on skin, or on clothing.
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P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P322
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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
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. 2927-71-1 ] {[proInfo.proName]}

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[ 2927-71-1 ] Synthesis Path-Downstream 1~8

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Fluorinated Building Blocks

Chlorides

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Pyrimidines

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