Water → HCID 86632759, compound

HRID 1923430Notes

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+].[NH2:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[C:22]([CH3:27])[N:21]=1.O>CC(N(C)C)=O>[NH2:19][C:20]1[N:21]=[C:22]([CH3:27])[CH:23]=[C:24]([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:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

812 mg (3.48 mmol) 2,2,2-trifluoro-N-(4-hydroxymethyl-benzyl)-acetamide is dissolved in 3 mL dry dimethylacetamide under argon atmosphere, and 167 mg (6.96 mmol) NaH is added over 5 min. 500 mg (3.48 mmol) 2-amino-4-chloro-6-methylpyrimidine 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 of 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). Yield: 350 mg (29%). ESI-MS m/z 341.7 [M+H]+.

Workup

customto quench all excess NaH
additionthe mixture poured into 50 ml of 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-162dc0427521410282dfb3f6a0fbc6b3
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178314B2

Reaction notes

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