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

HRID 1005727Notes

Reaction equation

HRID 1005727 reaction equation
O[C:2]1[C:3]2[S:11][CH:10]=[CH:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.O=P(Cl)(Cl)[Cl:14]>>[Cl:14][C:2]1[C:3]2[S:11][CH:10]=[CH:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178433427HCID 178433427, compound

Product 1

HCID 226744594-Chloro-2-methylthieno[3,2-d]pyrimidine

Procedure

A suspension of 4-hydroxy-2-methylthieno[3,2-d]pyrimidine (0.631 g, 3.8 mmol) in POCl3 (10 mL, 400 mmol) was refluxed for 4 h, concentrated in vacuo, treated with saturated NaHCO3 (20 mL), extracted with EtOAc (2×20 mL) and the combined extracts dried (MgSO4) and concentrated in vacuo to give the title compound (0.645 g, 92% as a pale yellow solid: mp 82-84° C.; IR νmax (Nujol)/cm−1 3073, 2925, 2855, 1566, 1515, 1460, 1378, 1344, 1307, 894 and 795; NMR δH (400 MHz, DMSO-d6) 3.41 (3H, s), 7.72 (1H, d, J 5.0 Hz) and 8.61 (1H, d, J 5.0 Hz).

Workup

  1. temperaturewas refluxed for 4 h
  2. concentrationconcentrated in vacuo
  3. additiontreated with saturated NaHCO3 (20 mL)
  4. extractionextracted with EtOAc (2×20 mL)
  5. dry with materialthe combined extracts dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93c0f52124fe4647a24fdd969ab284eb
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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