Water → HCID 24888159, compound

HRID 2375332Notes

Reaction equation

HRID 2375332 reaction equation
[CH3:1][CH:2]1[CH2:18][CH2:17][N:5]2[C:6](=[O:16])[CH:7]=[C:8]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)[N:9]=[C:4]2[NH:3]1.[H-].[Na+].[N:21]1[C:29]2[CH2:28][C@H:27]([CH2:30]OS(C)(=O)=O)[CH2:26][C:25]=2[CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[N:21]1[C:29]2[CH2:28][C@H:27]([CH2:30][N:3]3[C:4]4=[N:9][C:8]([C:10]5[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=5)=[CH:7][C:6](=[O:16])[N:5]4[CH2:17][CH2:18][CH:2]3[CH3:1])[CH2:26][C:25]=2[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 131726499HCID 131726499, compoundHCID 135797779HCID 135797779, compound

Product 1

HCID 24888159HCID 24888159, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 0.15 g (0.62 mmol) of 8-methyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one in 3 ml of anhydrous dimethylformamide was added 0.032 g (0.81 mmol) of sodium hydride (60% suspension in mineral oil). The mixture was allowed to stir at 50° C. for 30 min. 0.184 g (0.81 mmol) of methanesulfonic acid 6,7-dihydro-5H-[1]pyrindin-6-(R)-ylmethyl ester was added and the stirring continued at 85° C. for 18 h. Water was added and the mixture extracted with trichloromethane/methanol 90/10. The extracts were washed with a saturated aqueous solution of sodium chloride, dried and evaporated to give crude product. Purification by chromatography on silica gel, eluting with a mixture of ethyl acetate/ethanol in the proportions 100/0 to 74/26, gives 0.14 g (60%) of the compound in the form of free base. Mp.: 164-166° C.

Workup

  1. waitthe stirring continued at 85° C. for 18 h
  2. extractionthe mixture extracted with trichloromethane/methanol 90/10
  3. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  4. customdried
  5. customevaporated
  6. customto give crude product
  7. customPurification by chromatography on silica gel
  8. washeluting with a mixture of ethyl acetate/ethanol in the proportions 100/0 to 74/26

Sources & evidence

ORD record
ord-1620082b9f8c4d04a01ab83a4319db7e
Source dataset
uspto-grants-2008_12
Patent number
US07465737B2

Reaction notes

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