Water → HCID 86632762, compound

HRID 1923435Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1)=[O:4].[H-].[Na+].Cl[C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:23]=[C:22]([NH2:30])[N:21]=1.O>CC(N(C)C)=O>[NH2:30][C:22]1[N:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:25]=[C:20]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][NH:5][C:3](=[O:4])[C:2]([F:15])([F:16])[F:1])=[CH:8][CH:9]=2)[N:21]=1

Participants

Conditions

Temperature: 90 °C

Procedure

322 mg (1.38 mmol) 2,2,2-trifluoro-N-(4-hydroxymethyl-benzyl)-acetamide is dissolved in 2 mL dry dimethylacetamide under argon atmosphere, and 50 mg (2.1 mmol) NaH is added. 136 mg (0.69 mmol) 4-chloro-6-(trifluoromethyl)pyrimidin-2-amine 24 is then added and the solution stirred at 90° C. over night. 1 mL water is added carefully to quench all excess NaH and the mixture poured into 50 mL 0.5 N HCl. The crude product is extracted with ethyl acetate, the combined organic phases washed with brine and dried over MgSO4. After evaporation of the solvent, the product is purified by flash column chromatography (gradient ethyl acetate: cyclohexane from 1:1 to 3:1).

Workup

customto quench all excess NaH
additionthe mixture poured into 50 mL 0.5 N HCl
extractionThe crude product is extracted with ethyl acetate
washthe combined organic phases washed with brine
dry with materialdried over MgSO4
customAfter evaporation of the solvent
customthe product is purified by flash column chromatography (gradient ethyl acetate: cyclohexane from 1:1 to 3:1)

Sources & evidence

ORD record: ord-b788a053bc6c4e4987491877be128f08
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178314B2

Reaction notes

Loading…