Phosphorus oxychloride → 4-Chloro-2-methylthieno[3,2-d]pyrimidine

HRID 41357Notes

Reaction equation

HRID 41357 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=O)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.O=P(Cl)(Cl)[Cl:14]>>[Cl:14][C:4]1[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:2]([CH3:1])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1355858862-Methylthieno[3,2-d]pyrimidin-4(1H)-one2×

Product 1

HCID 226744594-Chloro-2-methylthieno[3,2-d]pyrimidineYield 88%

Procedure

2-Methylthieno[3,2-d]pyrimidin-4(3H)-one (compound 32b, 0.18 g, 1.13 mmol) was heated to 110° C. in POCl3 overnight. The solvent was removed under reduced pressure, and the residue was neutralized with saturated NaHCO3 solution. The product was extracted into CH2Cl2, and the organic phase separated, washed with brine, and dried (MgSO4). After removal of the solvent compound 32c was obtained as a yellow-orange solid (0.21 g, 88%). Compound 32c was used without further purification. Rf=0.16 (10% EtOAc/hexane). 1H NMR (400 MHz, DMSO-d6): δ 2.71 (s, 3H), 7.66 (d, J=5.6 Hz, 1H), 8.54 (d, J=5.6 Hz, 1H). LCMS 185 (M+H). Anal. (C23H29N8OF.0.35H2O.0.35 hexane) C, H, N. HPLC>98% purity.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionThe product was extracted into CH2Cl2
  3. customthe organic phase separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customAfter removal of the solvent compound 32c

Sources & evidence

ORD record
ord-69408e844e89462c97a6799595e2d3b1
Source dataset
uspto-grants-2013_09
Patent number
US08530652B2

Reaction notes

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