Dimethylformamide → 4-Chlorothieno[3,2-d]pyrimidine

HRID 50843Notes

Reaction equation

HRID 50843 reaction equation
CN(C=O)C.[Cl:6][CH:7](Cl)[CH3:8].C(Cl)(=O)C(Cl)=O.[N:16]1[C:21]2[CH:22]=[CH:23][S:24]C=2C(=O)[NH:18][CH:17]=1>O>[Cl:6][C:7]1[C:8]2[S:24][CH:23]=[CH:22][C:21]=2[N:16]=[CH:17][N:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63651,1-DichloroethaneHCID 65578Oxalyl chlorideHCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 27358214-Chlorothieno[3,2-d]pyrimidineYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of DMF (170.3 μL, 2.2 mmol) and dichloroethane (1.2 mL) at 0° C. under N2, oxalyl chloride (279.2 mg, 3.2 mmol) is added slowly and stirred for 10 min. 3H-thieno[3,2-d]pyrimid-4-one (152.2 mg, 1.0 mmol) is added and refluxed for 5 h. The reaction mixture is poured into water and extracted with CH2Cl2. The organic layer is stripped under reduced pressure to yield 4-chlorothieno[3,2-d]pyrimidine (140 mg, 82%) as a yellow solid. 1H NMR (DMSO) δ 9.05 (1H, s), 8.62 (1H, d, J=5 Hz), 7.79 (1H, d, J=5 Hz)

Workup

  1. temperaturerefluxed for 5 h
  2. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-4e2aeafd33734af78dfff5c9e8766ec8
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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