Acetic Acid → (+/-)-9-Benzylamino-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester hydrochloride

HRID 1890423Notes

Reaction equation

HRID 1890423 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([NH2:13])[C:10]2=[N:14][C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)=[CH:16][C:17](=[O:18])[N:9]2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl:51]CCl>>[ClH:51].[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([NH:13][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]2=[N:14][C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)=[CH:16][C:17](=[O:18])[N:9]2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 6344Dichloromethane2×HCID 5049666Sodium triacetoxyborohydrideHCID 669298339-amino-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4-a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester

Product 1

HCID 68736056(+/-)-9-Benzylamino-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester hydrochlorideYield 95%

Procedure

To a solution of 0.120 g (0.36 mmol) of 9-amino-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester in 3.6 ml of dichloromethane was added 0.041 g (0.38 mmol) of benzaldehyde, 0.192 g (0.91 mmol) of sodium triacetoxyborohydride and few drops of glacial acetic acid. The reaction mixture was stirred at room temperature for 15 hours. The residue was dissolved in dichloromethane and a saturated aqueous solution of sodium carbonate, extracted with dichloromethane and washed with saturated aqueous solution of sodium chloride, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 97/3/0.3 to give 0.145 g (95%) of pure product. The free base was transformed into its hydrochloride salt.

Workup

  1. extractiona saturated aqueous solution of sodium carbonate, extracted with dichloromethane
  2. washwashed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 97/3/0.3

Sources & evidence

ORD record
ord-ae0daa3ef2fe4bdeb54feb7b074ab8fb
Source dataset
uspto-grants-2013_08
Patent number
US08507476B2

Reaction notes

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