Phosphorus oxychloride → Acetic acid 4-chloro-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-ylmethyl ester

HRID 1056848Notes

Reaction equation

HRID 1056848 reaction equation
O[C:2]1[C:3]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:4]=2[N:5]=[C:6]([CH2:8][O:9][C:10](=[O:12])[CH3:11])[N:7]=1.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:2]1[C:3]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:4]=2[N:5]=[C:6]([CH2:8][O:9][C:10](=[O:12])[CH3:11])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178475918HCID 178475918, compound

Product 1

HCID 89713563Acetic acid 4-chloro-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-ylmethyl esterYield 85%

Procedure

The acetic acid 4-hydroxy-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-ylmethyl ester (4 g, 0.014 mol) in 20 ml of POCl3 was refluxed for 2 h. The excess of POCl3 was distilled off; the reaction mixture was quenched with ice, and extracted with ethyl acetate (3×25 ml). The combined organic layers were washed with bicarbonate solution, dried over anhydrous sodium sulphate, concentrated and dried to give acetic acid 4-chloro-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-ylmethyl ester (3.5 g, 85%) as brown solid. 1H NMR (400 MHz, CDCl3): δ 1.85-1.95 (m, 4H), 2.20 (s, 3H), 2.84-2.90 (m, 2H), 3.04-3.10 (m, 2H), 5.30 (s, 2H); LC-MS: [M+H]=297.2 & 299.1 m/z.

Workup

  1. distillationThe excess of POCl3 was distilled off
  2. customthe reaction mixture was quenched with ice
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. washThe combined organic layers were washed with bicarbonate solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-ee30009dc94744a28d0e0e21c6a9cd9e
Source dataset
uspto-grants-2016_07
Patent number
US09399647B2

Reaction notes

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