Water → HCID 24986454, compound

HRID 217886Notes

Reaction equation

HRID 217886 reaction equation
[NH2:1][CH:2]1[C:7]2=[N:8][C:9]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:10][C:11](=[O:12])[N:6]2[CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:26][N:27]1[C:31]2[CH:32]=[CH:33][C:34]([C:36](Cl)=[O:37])=[CH:35][C:30]=2[N:29]=[N:28]1.O>O1CCCC1>[CH3:26][N:27]1[C:31]2[CH:32]=[CH:33][C:34]([C:36]([NH:1][CH:2]3[C:7]4=[N:8][C:9]([C:13]5[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=5)=[CH:10][C:11](=[O:12])[N:6]4[CH2:5][CH2:4][CH2:3]3)=[O:37])=[CH:35][C:30]=2[N:29]=[N:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27765501-Methyl-1h-1,2,3-benzotriazole-5-carbonyl chlorideHCID 67265741HCID 67265741, compound

Product 1

HCID 24986454HCID 24986454, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.050 g (0.21 mmol) of (+/−)9-amino-2-pyridin -4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one dissolved in 2.2 mL of tetrahydrofuran was added 30 μl (0.25 mmol) of triethylamine and 0.0484 g (0.25 mmol) of 1-methyl-1H-1,2,3-benzotriazole-5-carbonyl chloride. The resulting mixture was stirred at room temperature for 16 h. Water was added and the mixture extracted with ethyl acetate. The extracts were washed with a saturated aqueous solution of ammonium chloride, dried and evaporated. The residue was purified by silica gel chromatography, eluting with dichloromethane/methanol/ammonia in the proportions 95/5/0.5 to give 0.041 g of pure product obtained in the form of free base.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe extracts were washed with a saturated aqueous solution of ammonium chloride
  3. customdried
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with dichloromethane/methanol/ammonia in the proportions 95/5/0.5

Sources & evidence

ORD record
ord-2ac0c5045780416abe07a20d3cea8703
Source dataset
uspto-grants-2012_06
Patent number
US08198287B2

Reaction notes

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