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

HRID 1386224Notes

Reaction equation

HRID 1386224 reaction equation
CN(C=O)C.[CH2:6]([Cl:8])Cl.C(Cl)(=O)C(Cl)=O.[N:15]1[C:20]2[S:21][CH:22]=[CH:23][C:19]=2C(=O)[NH:17][CH:16]=1>O>[Cl:8][C:6]1[C:19]2[CH:23]=[CH:22][S:21][C:20]=2[N:15]=[CH:16][N:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 2808547thieno(2,3-d)pyrimidin-4(3H)-one

Product 1

HCID 7366184-Chlorothieno[2,3-d]pyrimidineYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of DMF (90 μL) and CH2Cl2 (2 mL) at 0° C. under N2, oxalyl chloride (148 mg, 1.2 mmol) is added slowly and stirred for 10 min. 3H-Thieno[2,3-d]pyrimid-4-one (81 mg, 0.52 mmol) is added as a solid to the solution and warmed with a heat gun until the solid dissolves. The reaction is stirred at 25° C. for 12 h under N2. The reaction mixture is poured into water and extracted with CH2Cl2 . The phases are separated and the organic layer is dried (Na2SO4) and stripped under reduced pressure to yield 4-chlorothieno[2,3-d]pyrimidine (87.6 mg, 97%) as a solid. 1H NMR (DMSO) δ 8.96 (1H, s), 8.17 (1H, d, J=6.0 Hz), 7.62 (1H, d, J=6.0 Hz).

Workup

  1. temperaturewarmed with a heat gun until the solid
  2. dissolutiondissolves
  3. stirringThe reaction is stirred at 25° C. for 12 h under N2
  4. extractionextracted with CH2Cl2
  5. customThe phases are separated
  6. dry with materialthe organic layer is dried (Na2SO4)

Sources & evidence

ORD record
ord-6a9e927e88004e5caa9e669e18db812f
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

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