Acetyl chloride → HCID 18473284, compound

HRID 1937402Notes

Reaction equation

HRID 1937402 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[CH:17]=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:20](Cl)(=[O:22])[CH3:21]>C(#N)C>[C:2]1([CH3:1])[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]2[C:10]3[CH:17]=[CH:16][N:15]([C:20](=[O:22])[CH3:21])[C:11]=3[N:12]=[CH:13][N:14]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 18473273HCID 18473273, compound

Product 1

HCID 18473284HCID 18473284, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (3-methyl-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine (0.75 g, 3.4 mmol) dissolved in hot acetonitrile (30 ml) was added sodium hydride (0.16 g, 4.0 mmol, 60% dispersion in mineral oil). After stirring at ambient temperature for 0.75 hours, acetyl chloride (0.48 ml, 6.7 mmol) was added and stirring continued for 48 hours. The reaction mixture was concentrated in vacuo, triturated in hot ethyl acetate, and filtered. The filtrate was concentrated in vacuo to give an orange solid residue. The solid was purified by flash chromatography on silica gel (13 g,40 mm mesh) using 1:3 ethyl acetate/hexanes to afford 1-(4-m-tolylamino-pyrrolo[2,3-d]pyrimidin-7-yl)-ethanone as a yellow solid (0.21 g). TS-MS: 309 (MH+); anal. RP18-HPLC RT: min.

Workup

  1. stirringstirring
  2. waitcontinued for 48 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customtriturated in hot ethyl acetate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give an orange solid residue
  8. customThe solid was purified by flash chromatography on silica gel (13 g,40 mm mesh)

Sources & evidence

ORD record
ord-3117b2bb3ed84f579becd9a07e77744f
Source dataset
uspto-grants-2002_05
Patent number
US06395733B1

Reaction notes

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