Sodium hydride → HCID 24887948, compound

HRID 2375334Notes

Reaction equation

HRID 2375334 reaction equation
[CH3:1][C:2]1([CH3:19])[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:22]1[C:30]2[CH2:29][C@H:28]([CH2:31]OS(C)(=O)=O)[CH2:27][C:26]=2[CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>CN(C)C=O>[N:22]1[C:30]2[CH2:29][C@H:28]([CH2:31][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][C:2]3([CH3:19])[CH3:1])[CH2:27][C:26]=2[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 131726499HCID 131726499, compoundHCID 135556071HCID 135556071, compound

Product 1

HCID 24887948HCID 24887948, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 0.226 g (0.88 mmol) of 8,8-dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one in 5 ml of anhydrous dimethylformamide was added 0.040 g (0.97 mmol) of sodium hydride (60% suspension in mineral oil) and the mixture was allowed to stir at 45° C. for 3 hours. 0.20 g (0.88 mmol) of methanesulfonic acid 6,7-dihydro-5H-[1]pyrindin-6-(R)-ylmethyl ester was added and the stirring continued at 80° C. for 18 h. The mixture was cooled and a solution of saturated ammonium chloride was added. The mixture was 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 70/20, gives 0.197 g (58%) of the compound in the form of free base. Mp.: 202-204° C.

Workup

  1. waitthe stirring continued at 80° C. for 18 h
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was extracted with trichloromethane/methanol 90/10
  4. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  5. customdried
  6. customevaporated
  7. customto give crude product
  8. customPurification by chromatography on silica gel eluting
  9. additionwith a mixture of ethyl acetate/ethanol in the proportions 100/0 to 70/20

Sources & evidence

ORD record
ord-f7be09e73f0040feb0650fd843d02b95
Source dataset
uspto-grants-2008_12
Patent number
US07465737B2

Reaction notes

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