Water → HCID 22674450, compound

HRID 1005708Notes

Reaction equation

HRID 1005708 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:13]1[C:14]2[S:25][CH:24]=[CH:23][C:15]=2[N:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:18]=1.O>CN(C=O)C.C1(C)C=CC=CC=1>[C:3]1([CH:9]([C:13]2[C:14]3[S:25][CH:24]=[CH:23][C:15]=3[N:16]=[C:17]([C:19]([F:21])([F:22])[F:20])[N:18]=2)[C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8794PhenylacetonitrileHCID 24758Sodium hydrideHCID 226743734-Chloro-2-(trifluoromethyl)thieno[3,2-d]pyrimidine

Product 1

HCID 22674450HCID 22674450, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Procedure

A suspension of NaH (60% dispersion in oil, 60 mg, 1.5 mmol) in DMF (5 mL) and toluene (15 mL) at room temperature was treated with phenylacetonitrile (0.16 g, 1.37 mmol), stirred for 10 min, treated with a solution of 4-chloro-2-trifluoromethylthieno[3,2-d]pyrimidine (0.3 g, 126 mmol) in DMF (2 mL), stirred for 15 min, treated with water (5 mL) and the phases separated. The aqueous phase was extracted with EtOAc (2×50 mL), the combined organic phase washed with water (3×10 mL), brine (10 mL), dried (MgSO4), concentrated in vacuo and the resulting orange oily solid crystallised from heptane to give the title compound (0.1 g, 25%) as a gold solid.

Workup

  1. stirringstirred for 15 min
  2. customthe phases separated
  3. extractionThe aqueous phase was extracted with EtOAc (2×50 mL)
  4. washthe combined organic phase washed with water (3×10 mL), brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe resulting orange oily solid crystallised from heptane

Sources & evidence

ORD record
ord-0ac320fbca184228b536aa8e1713e0e6
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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