Dimethylformamide → HCID 66642837, compound

HRID 869237Notes

Reaction equation

HRID 869237 reaction equation
Cl[C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([NH:11][C:12]2[CH:13]=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:5]=[C:4]([S:22][CH3:23])[N:3]=1.[C:24]([O-:27])(=[O:26])[CH3:25].[Na+].CN(C=O)C>O>[C:24]([O:27][C:2]1[C:7]([C:8](=[O:9])[NH2:10])=[C:6]([NH:11][C:12]2[CH:13]=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:5]=[C:4]([S:22][CH3:23])[N:3]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 86662045HCID 86662045, compound

Product 1

HCID 66642837HCID 66642837, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-chloro-2-(methylsulfanyl)-6-(quinolin-3-ylamino)pyrimidine-5-carboxamide (Preparation Example 344) (0.68 g) and sodium acetate (0.80 g), DMF (7 mL) was added and stirred at 100° C. for 6 hours. After the reaction liquid was returned to room temperature, water was added, and the resulting solid was collected by filtration to give 5-carbamoyl-2-(methylsulfanyl)-6-(quinolin-3-ylamino)pyrimidin-4-yl acetate (0.71 g).

Workup

  1. additionwas added
  2. customAfter the reaction liquid
  3. customwas returned to room temperature
  4. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-d70306db52874d9783938242ed017b3b
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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