Dimethylformamide → 3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-[(3-pyridyl)methyl]pyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1858202Notes

Reaction equation

HRID 1858202 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:15][CH:16]=2)[NH:11][C:10]1=[O:23].[H-].[Na+].Cl.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1CCl.[CH3:35]N(C)C=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:15][CH:16]=2)[N:11]([CH2:35][C:31]2[CH:32]=[N:27][CH:28]=[CH:29][CH:30]=2)[C:10]1=[O:23]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 23392Picolyl chloride hydrochlorideHCID 24758Sodium hydrideHCID 221250983-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 221250103-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-[(3-pyridyl)methyl]pyrimido[4,5-d]pyrimidin-2(1H)-oneYield 48%

Conditions

Temperature
100 °C

Procedure

An ice-cooled solution of 100 mg (0.27 mmol) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one in 6 ml of dimethylformamide was treated with 22 mg (0.54 mmol) of sodium hydride (60% w/w). After 30 minutes the mixture was treated with 50 mg (0.3 mmol) of picolyl chloride hydrochloride and then heated to 90° C. for 2 hours and to 100° C. for a further hour. The mixture was evaporated and the residue was treated with 30 ml of dichloromethane and 30 ml of water. The phases were separated and the organic phase was washed with 30 ml of water, dried over magnesium sulfate, filtered and evaporated to give 60 mg (48%) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-[(3-pyridyl)methyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a yellow solid.

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was treated with 30 ml of dichloromethane and 30 ml of water
  3. customThe phases were separated
  4. washthe organic phase was washed with 30 ml of water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e0b08cf605614fcaaee647a18b5dd68b
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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