Phosphorus oxychloride → HCID 10823553, compound

HRID 1489613Notes

Reaction equation

HRID 1489613 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2=[N:9][C:10]3[C:15]([C:14](=O)[NH:13][CH2:12][N:11]=3)=[C:5]2[CH:4]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:14]1[C:15]2[C:5]3[C:6](=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:9][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 70025343HCID 70025343, compound

Product 1

HCID 10823553HCID 10823553, compoundYield 81%

Conditions

Temperature
90 °C

Procedure

A suspension of 6-methoxy-3H-indolo[2,3-d]pyrimidine-4-one (800 mg, 3.08 mmol, ~83% pure) and POCl3 (7 mL) is heated at 90° C. for 6 h. The suspension is concentrated to a solid that is evacuated at 1 mm for 1 h. The solids are cooled in a -78° C. bath then treated dropwise with cold H2O. The bath is removed and the frozen solids are allowed to gradually melt. The solids are filtered, washed well with cold H2O, and dried to leave 4-chloro-6-methoxyindolo[2,3-d]pyrimidine (733 mg, 81%) that is about 80% pure. 1H NMR (DMSO): δ12.64 (1H, br s, exchanges with D2O), 8.74 (1H, s), 7.74 (1H, d, J=2.4 Hz), 7.57 (1H, d, J=8.9 Hz), 7.28 (1H, dd, J=8.9, 2.4 Hz), 3.88 (3H, s).

Workup

  1. concentrationThe suspension is concentrated to a solid
  2. customthat is evacuated at 1 mm for 1 h
  3. temperatureThe solids are cooled in a -78° C. bath
  4. additionthen treated dropwise with cold H2O
  5. customThe bath is removed
  6. filtrationThe solids are filtered
  7. washwashed well with cold H2O
  8. customdried

Sources & evidence

ORD record
ord-e09b39881be24efcba32179480036206
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

Loading…