Water → (+/-)-9-(2,3-Dihydro-benzofuran-2-ylmethyl)-7,7-dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

HRID 2375326Notes

Reaction equation

HRID 2375326 reaction equation
CC1(C)CN2C(=[O:17])C=C(C3C=CN=CC=3)N=C2NC1.[H-].[Na+].N1[C:30]2[CH2:29][C@H:28]([CH2:31][N:32]3[C:37]4=[N:38][C:39]([C:43]5[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=5)=[CH:40][C:41](=[O:42])[N:36]4[CH2:35][C:34]([CH3:50])([CH3:49])[CH2:33]3)[CH2:27][C:26]=2[CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[O:17]1[C:30]2[CH:29]=[CH:23][CH:24]=[CH:25][C:26]=2[CH2:27][CH:28]1[CH2:31][N:32]1[C:37]2=[N:38][C:39]([C:43]3[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=3)=[CH:40][C:41](=[O:42])[N:36]2[CH2:35][C:34]([CH3:49])([CH3:50])[CH2:33]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12073797(+)-(6R)-9-(6,7-Dihydro-5H-[1]pyrindin-6-ylmethyl)-7,7-dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-oneHCID 1357386167,7-Dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

Product 1

HCID 12073800(+/-)-9-(2,3-Dihydro-benzofuran-2-ylmethyl)-7,7-dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-oneYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

A suspension of 0.51 g (2 mmol) of 7,7-dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one in 10 ml of anhydrous dimethylformamide was treated with 96 mg (2 mmol) of sodium hydride (50% suspension in mineral oil) and the resulting mixture was stirred at 40° C. for 40 min. 0.52 g (2 mmol) of (+/−)2-iodomethyl-2,3-dihydro-benzofuran (prepared according to Synthesis 1997, (1), 23-25) in 2 ml of anhydrous dimethylformamide was added and the reaction mixture stirred at 60° C. for 20 min. The solution was treated with water and extracted with ethyl acetate. The organic phase was dried and evaporated to give crude product, which was purified by silica gel chromatography, eluting with dichloromethane/methanol/ammonia in the proportions 99/1/0.1 to 98/2/0.2 to give 0.171 g of pure product obtained in the form of free base. Mp: 147-149° C.

Workup

  1. stirringthe reaction mixture stirred at 60° C. for 20 min
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. customevaporated
  5. customto give crude product, which
  6. customwas purified by silica gel chromatography
  7. washeluting with dichloromethane/methanol/ammonia in the proportions 99/1/0.1 to 98/2/0.2

Sources & evidence

ORD record
ord-3ae3c9d82e9347b79ba211e4860fef88
Source dataset
uspto-grants-2008_12
Patent number
US07465737B2

Reaction notes

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