Phosphorus oxychloride → HCID 59447941, compound

HRID 1916287Notes

Reaction equation

HRID 1916287 reaction equation
O[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15]#[N:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:5]=[CH:4][N:3]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15]#[N:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178509462HCID 178509462, compound

Product 1

HCID 59447941HCID 59447941, compound

Procedure

A solution of 4-hydroxy-9H-pyrimido[4,5-b]indole-7-carbonitrile (215 mg, 1.02 mmol) in 5 mL POCl3 (5 mL) was heated at 100° C. for 18 hours. Upon cooling to room temperature the reaction mixture was evaporated to dryness and the residue treated with saturated sodium bicarbonate solution and ethyl acetate. The organic phase was dried over sodium sulphate and concentrated to the title compound as an orange solid. LC-MS (1) Rt 1.66 min; (100% UV), m/z (ES−) 227/229. The product was used without further purification.

Workup

  1. customwas evaporated to dryness
  2. additionthe residue treated with saturated sodium bicarbonate solution and ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated to the title compound as an orange solid
  5. customThe product was used without further purification

Sources & evidence

ORD record
ord-20d4db49d38b4919b4b60ff12dad09d5
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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