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

HRID 2297752Notes

Reaction equation

HRID 2297752 reaction equation
CN(C)C=O.[C:6]([Cl:11])(=O)[C:7](Cl)=O.[N:12]1[C:17]2[CH:18]=[CH:19][S:20]C=2C(=O)[NH:14][CH:13]=1.O>ClC(Cl)C>[Cl:11][C:6]1[C:7]2[S:20][CH:19]=[CH:18][C:17]=2[N:12]=[CH:13][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 27358214-Chlorothieno[3,2-d]pyrimidineYield 76%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dimethyl formamide (6.6 mL, 85.4 mmol) in 50 mL of dichloroethane was cooled to 0° C. and oxalyl chloride (62 mL, 124 mmol, 2M in dichloromethane) was added slowly over several minutes forming a white gel. 3H-thieno[3,2-d]pyrimidin-4-one (5.90 g, 38.8 mmol) was added and the reaction mixture was heated to reflux. After 2.5 hours the mixture was cooled to room temperature and poured into water. The product was extracted into dichloromethane (3×100 mL), dried over sodium sulfate, and concentrated in vacuo to afford 5.01 g (76%) of 4-chloro-thieno[3,2-d]pyrimidine. 1H NMR (400 MHz, DMSO) d 8.99 (s, 1H), 8.55 (d, 1H), 7.71 (d, 1H). LC-MS: 171 (MH+); HPLC RT: 2.85 minutes.

Workup

  1. customforming a white gel
  2. temperaturethe reaction mixture was heated to reflux
  3. extractionThe product was extracted into dichloromethane (3×100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fea64385910443082d89662d9272031
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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