Water → 4-Chloro-2-amino-6-[1-(2-trifluoromethylphenyl)-2,2,2-trifluoro-ethoxy]-pyrimidine

HRID 469842Notes

Reaction equation

[H-].[Na+].[F:3][C:4]([F:18])([F:17])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([OH:16])[C:12]([F:15])([F:14])[F:13].[NH2:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[C:22]([Cl:27])[N:21]=1.O>C1COCC1.C(OCC)(=O)C>[Cl:27][C:22]1[CH:23]=[C:24]([O:16][CH:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([F:17])([F:18])[F:3])[C:12]([F:13])([F:14])[F:15])[N:25]=[C:20]([NH2:19])[N:21]=1

Participants

Conditions

Temperature: 70 °C

Procedure

NaH (80 mg, 60%, 3.0 mmol) was added to a solution of 1-(2-trifluoromethylphenyl)-2,2,2-trifluoro-ethanol (244 mg, 1 mmol) in 10 ml of anhydrous THF. The mixture was stirred for 20 minutes, 2-amino-4,6-dichloro-pyrimidine (164 mg, 1 mmol) was added and then the reaction mixture was heated at 70° C. for 1 hour. After cooling, 5 ml water was added and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to give 267 mg of 4-chloro-6-[2,2,2-trifluoro-1-(2-trifluoromethylphenyl)-ethoxy]-pyrimidin-2-ylamine, yield 71%.

Workup

temperatureAfter cooling
extractionto extract the product
dry with materialThe organic layer was dried over sodium sulfate
customThe solvent was removed by rotovap

Sources & evidence

ORD record: ord-9d2825698b324c3cbe2e95646bbb465d
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629156B2

Reaction notes

Loading…