Phosphorus oxychloride → HCID 10823553, compound

HRID 1358294Notes

Reaction equation

HRID 1358294 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, compound

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 dine (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-904f9966ad6a4a4e80597abafc8239c6
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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