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

HRID 254741

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:15])[C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1.[NH2:16][C:17]1[N:22]=[C:21](Cl)[CH:20]=[C:19]([Cl:24])[N:18]=1.O>C1COCC1.C(OCC)(=O)C>[Cl:24][C:19]1[CH:20]=[C:21]([O:15][CH:10]([C:7]2[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][CH:6]=2)[C:11]([F:12])([F:13])[F:14])[N:22]=[C:17]([NH2:16])[N:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

NaH (80 mg, 60%, 3.0 mmol) was added to a solution of 1-(4-methylphenyl)-2,2,2-trifluoro-ethanol (190 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 209 mg of 4-chloro-6-[1-(4-methylphenyl)-2,2,2-trifluoro-ethoxy]-pyrimidin-2-ylamine, yield 66%.

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-09848a0aa3ce42c6a01a3d4fbecf0922
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875622B2

Linked notes

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