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

HRID 2287758Notes

Reaction equation

HRID 2287758 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-70e2ab5e1cbd4c2b9c1e48f5a123e474
Source dataset
uspto-grants-2000_07
Patent number
US06084095

Reaction notes

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