Phosphorus oxychloride → 4-Chloro-6,7,8,9-tetrahydrobenzofuro[3,2-D]pyrimidine

HRID 1428237Notes

Reaction equation

HRID 1428237 reaction equation
[N:1]1[C:6]2[C:7]3[CH2:13][CH2:12][CH2:11][CH2:10][C:8]=3[O:9][C:5]=2[C:4](O)=[N:3][CH:2]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:4]1[C:5]2[O:9][C:8]3[CH2:10][CH2:11][CH2:12][CH2:13][C:7]=3[C:6]=2[N:1]=[CH:2][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785179296,7,8,9-tetrahydro-1H-[1]benzofuro[3,2-d]pyrimidin-4-one

Product 1

HCID 866287414-Chloro-6,7,8,9-tetrahydrobenzofuro[3,2-D]pyrimidine

Conditions

Temperature
110 °C

Procedure

A 15 mL sealed tube was charged with 6,7,8,9-tetrahydro-benzo[4,5]furo[3,2-d]pyrimidin-4-ol (0.31 g, 1.6 mmol) and POCl3 (3 mL), sealed, and heated to 110° C. After 30 min, POCl3 was removed under reduced pressure and the resultant residue was purified by FCC (40% EtOAc/hexanes) to afford the desired product as a white solid (0.27 g). MS: 189.0 (negative mode). 1H NMR (400 MHz, d6-DMSO) δ ppm 8.00 (s, 1H), 2.74-2.67 (m, 2H), 2.57-2.51 (m, 2H), 1.90-1.82 (m, 2H), 1.80-1.70 (m, 2H).

Workup

  1. customA 15 mL sealed tube
  2. customsealed
  3. customPOCl3 was removed under reduced pressure
  4. customthe resultant residue was purified by FCC (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-93df2d6f2071490fb43e2e46e85c3f97
Source dataset
uspto-grants-2015_01
Patent number
US08937075B2

Reaction notes

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