Water → 5-chloro-N-(3-(trifluoromethyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine

HRID 1410103

Reaction equation

HRID 1410103 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[F:12][C:13]([F:22])([F:21])[C:14]1[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=1.CCN(C(C)C)C(C)C.O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:21])[F:22])[CH:15]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73753-(Trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 6096395,7-Dichlorothiazolo(5,4-d)pyrimidine

Product 1

HCID 866717905-chloro-N-(3-(trifluoromethyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 5,7-dichlorothiazolo[5,4-d]pyrimidine (300 mg, 1.45 mmol) and 3-(trifluoromethyl)benzenamine (304.8 mg, 1.89 mmol) in 10 mL of DMSO was added DIEA (282 mg, 2.18 mmol) in one portion at room temperature. Then the reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into 40 mL of water, and the solid obtained was filtered, rinsed with water, and dried. The desired product 5-chloro-N-(3-(trifluoromethyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine was obtained (356 mg, 74%) as a yellow solid. LC-MS: 331.0 [M+H]+, tR=1.70 min.

Workup

  1. customthe solid obtained
  2. filtrationwas filtered
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-20d8d7f7243a46feb4e52695103c439e
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Linked notes

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