Oxalyl chloride → 4-(3-Ethynyl-phenylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic Acid Methyl Ester Hydrochloride

HRID 1937403Notes

Reaction equation

HRID 1937403 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:11]3[C:18]([C:19]([OH:21])=[O:20])=[CH:17][NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].[C:22](Cl)(=O)C([Cl:25])=O>C(Cl)Cl.CN(C=O)C>[ClH:25].[CH3:22][O:20][C:19]([C:18]1[C:11]2[C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[CH:2])[CH:4]=3)=[N:15][CH:14]=[N:13][C:12]=2[NH:16][CH:17]=1)=[O:21]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 224608344-(3-Ethynyl-phenylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic Acid

Product 1

HCID 867580994-(3-Ethynyl-phenylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic Acid Methyl Ester HydrochlorideYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To 4-(3-ethynyl-phenylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (0.108 g, 0.39 mmol) in dry methylene chloride (2 ml) was added a solution of oxalyl chloride (0.17 ml, 1.9 mmol) in dry methylene chloride (4 ml) followed by 1 drop of dry DMF. The suspension was stirred at ambient temperature for 1 hour, then concentrated in vacuo. To the resulting solid was added dry acetone (2 ml) and dry methanol (1 ml). The solution was stirred at ambient temperature for 15 hours, then concentrated in vacuo. The residue was diluted with ethyl acetate and water, and the solid filtered and dried in vacuo to afford the title compound as a tan powder (40 mg, 35%). TS-MS: 293 (MH+); anal. RP18-HPLC RT: min.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the resulting solid was added dry acetone (2 ml) and dry methanol (1 ml)
  3. stirringThe solution was stirred at ambient temperature for 15 hours
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with ethyl acetate and water
  6. filtrationthe solid filtered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f310ae886dbb476d97de1426a77228fa
Source dataset
uspto-grants-2002_05
Patent number
US06395733B1

Reaction notes

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