4-Toluenesulfonyl chloride → HCID 86760496, compound

HRID 1766069Notes

Reaction equation

HRID 1766069 reaction equation
[C:1]([NH:5][C:6]([C:8]1[S:25][C:11]2[N:12]=[C:13]([S:23][CH3:24])[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=3)[C:10]=2[C:9]=1[NH2:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>N1C=CC=CC=1.C(Cl)Cl>[C:1]([NH:5][C:6]([C:8]1[S:25][C:11]2[N:12]=[C:13]([S:23][CH3:24])[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][S:33]([C:30]4[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=4)(=[O:35])=[O:34])[CH:17]=3)[C:10]=2[C:9]=1[NH2:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 59641628HCID 59641628, compound

Product 1

HCID 86760496HCID 86760496, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 5-amino-2-methylthio-4-(3-aminophenyl)-thieno[2,3-d]pyrimidine-6-carboxamide (example 9e, 100 mg) was dissolved in dry pyridine (5 ml). p-Toluenesulfonyl chloride (70 mg) was added and the mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with CH2Cl2 and washed with 0.1M aq. HCl. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with hept/EtOAc=3/2 (v/v) as eluent.

Workup

  1. washwashed with 0.1M aq. HCl
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe title compound was purified by chromatography on silica gel with hept/EtOAc=3/2 (v/v) as eluent

Sources & evidence

ORD record
ord-dc0fca87e9b444c4a0e4263c4cc943cc
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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