Acetyl chloride → HCID 58938663, compound

HRID 598191Notes

Reaction equation

HRID 598191 reaction equation
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])=[CH:12][NH:11][C:9]=2[N:10]=1)[CH2:2][CH3:3].[H-].[Na+].[C:30](Cl)(=[O:32])[CH3:31]>C(#N)C.O>[C:30]([N:11]1[C:9]2[N:10]=[C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:25][CH2:26][CH3:27])[N:6]([CH3:24])[C:7](=[O:23])[C:8]=2[C:13]([C:14]2[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=2[CH3:20])=[CH:12]1)(=[O:32])[CH3:31]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 58938618HCID 58938618, compound

Product 1

HCID 58938663HCID 58938663, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-(dipropylamino)-5-mesityl-3-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (20 mg, 0.054 mmol) in acetonitrile (1.5 ml) was added sodium hydride (60% in oil, 5 mg, 0.125 mmol) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 0.5 hour, to the mixture was added a solution of acetylchloride (20 mg, 0.25 mmol) and acetonitrile (0.5 ml) at 0° C. and stirred for 0.5 hour. After stirring at 80° C. for 1 hour, the mixture was diluted with water (20 ml) and extracted with ethyl acetate (20 ml×3). The extracts were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (10:1) to give 17 mg (77%) of the title compound.

Workup

  1. stirringAfter stirring at room temperature for 0.5 hour, to the mixture
  2. stirringstirred for 0.5 hour
  3. stirringAfter stirring at 80° C. for 1 hour
  4. extractionextracted with ethyl acetate (20 ml×3)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-168858adef9f4d0390fd5ddc119b52eb
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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