Phosphorus oxychloride → 1-chloro-6-methyl-N-(3-(6-(methylamino)pyrimidin-4-yl)pyridin-2-yl)isoquinolin-5-amine

HRID 2092289Notes

Reaction equation

HRID 2092289 reaction equation
[CH3:1][C:2]1[C:3]([NH:13][C:14]2[C:19]([C:20]3[CH:25]=[C:24]([NH:26][CH3:27])[N:23]=[CH:22][N:21]=3)=[CH:18][CH:17]=[CH:16][N:15]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[NH:7][CH:6]=[CH:5]2.O=P(Cl)(Cl)[Cl:30]>>[Cl:30][C:8]1[C:9]2[CH:10]=[CH:11][C:2]([CH3:1])=[C:3]([NH:13][C:14]3[C:19]([C:20]4[CH:25]=[C:24]([NH:26][CH3:27])[N:23]=[CH:22][N:21]=4)=[CH:18][CH:17]=[CH:16][N:15]=3)[C:4]=2[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 589422616-methyl-5-(3-(6-(methylamino)pyrimidin-4-yl)pyridin-2-ylamino)isoquinolin-1(2H)-one

Product 1

HCID 589422651-chloro-6-methyl-N-(3-(6-(methylamino)pyrimidin-4-yl)pyridin-2-yl)isoquinolin-5-amine

Conditions

Temperature
120 °C

Procedure

6-Methyl-5-(3-(6-(methylamino)pyrimidin-4-yl)pyridin-2-ylamino)isoquinolin-1(2H)-one (195 mg, 0.54 mmol) was suspended in POCl3 (10 mL) and heated at 120° C. for 3 h. POCl3 was removed in vacuo and the residue was washed with toluene three times. The residue was added to water and the resulting solid collected by filtration, washing with saturated aqueous sodium bicarbonate and water. The resulting title compound was dried in vacuo. MS (M+H)+ 377.

Workup

  1. customPOCl3 was removed in vacuo
  2. washthe residue was washed with toluene three times
  3. additionThe residue was added to water
  4. filtrationthe resulting solid collected by filtration
  5. washwashing with saturated aqueous sodium bicarbonate and water
  6. dry with materialThe resulting title compound was dried in vacuo

Sources & evidence

ORD record
ord-5c6a0c6a745c486790d83a8708317714
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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