Water → HCID 86632758, compound

HRID 1923428Notes

Reaction equation

HRID 1923428 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]=[CH:22][N:21]=1.O>CC(N(C)C)=O>[NH2:19][C:20]1[N:25]=[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)[CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2233322-Amino-4-chloropyrimidineHCID 15852209N-(4-Hydroxymethylbenzyl)trifluoroacetamide

Product 1

HCID 86632758HCID 86632758, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

252 mg (1.15 mmol) 2,2,2-trifluoro-N-(4-hydroxymethyl-benzyl)-acetamide is dissolved in 2 mL dry dimethylacetamide under argon atmosphere, and 56 mg (2.31 mmol) NaH is added. 100 mg (0.77 mmol) 2-amino-4-chloro-pyrimidine (2) is added and the solution stirred at room temperature 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 (ethyl acetate:cyclohexane 1:1). Yield: 160 mg (63%). ESI-MS m/z 327.4 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-f4748bf2fd054e70ad14b512882ffd0e
Source dataset
uspto-grants-2012_05
Patent number
US08178314B2

Reaction notes

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