Dimethylformamide → HCID 59643072, compound

HRID 2251090Notes

Reaction equation

HRID 2251090 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[CH:10]=[C:9]2[C:19]([OH:21])=O)=[CH:4][CH:3]=1.CN(C=O)C.C(Cl)(=O)C([Cl:30])=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[CH:10]=[C:9]2[C:19]([Cl:30])=[O:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 59643085HCID 59643085, compound

Product 1

HCID 59643072HCID 59643072, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of 7-(4-fluoro-phenyl)-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid, 24, (4.7 g, 15.5 mmol) in dichloromethane (100 mL) is added DMF (0.5 mL) followed by dropwise addition of oxalyl chloride (2.7 mL, 31.1 mmol). The mixture is allowed to slowly warm to room temperature over a period of 3 hours. The reaction mixture is concentrated in vacuo and can be dried azeotropically with toluene to afford 4.7 g of the desired product, which is used without further purification: 1H NMR (300 MHz, CDCl3) δ 9.38 (s, 1H), 8.04 (s, 1H), 7.40-7.20 (m, 4H), 2.58 (s, 3H); ESI+ MS: m/z (rel intensity) 322.0 (100, M++H).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dry with materialcan be dried azeotropically with toluene

Sources & evidence

ORD record
ord-c7bef2d2d73d47fc8a7e7b6bc07c0b54
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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