Water → HCID 86632760, compound

HRID 1923432Notes

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]([Cl:27])[N:21]=1.O>CC(N(C)C)=O>[NH2:19][C:20]1[N:21]=[C:22]([Cl: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

356 mg (1.52 mmol) 2,2,2-trifluoro-N-(4-hydroxymethyl-benzyl)-acetamide is dissolved in 3 mL dry dimethylacetamide under argon atmosphere, and 73.1 mg (3.1 mmol) NaH is added. 250 mg-(1.54 mmol) 2-amino-4,6-dichloropyrimidine 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). Yield: 254 mg (46%). ESI-MS m/z 361.1 [M+H]+.

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-17fd165307a544208c2b6e8320a3ff9f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178314B2

Reaction notes

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