Acetic Acid → (+/-) 9-[(Pyridin-2-ylmethyl)-amino]-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4-a-diaza-benzocyclohepten-4-one

HRID 1886968Notes

Reaction equation

HRID 1886968 reaction equation
[NH2:1][CH:2]1[C:8]2=[N:9][C:10]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][N:15]=3)=[CH:11][C:12](=[O:13])[N:7]2[CH2:6][CH2:5][O:4][CH2:3]1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][NH:1][CH:2]1[C:8]2=[N:9][C:10]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][N:15]=3)=[CH:11][C:12](=[O:13])[N:7]2[CH2:6][CH2:5][O:4][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 142732-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68626960HCID 68626960, compound

Product 1

HCID 44160105(+/-) 9-[(Pyridin-2-ylmethyl)-amino]-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4-a-diaza-benzocyclohepten-4-oneYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.090 g (0.35 mmol) of (+/−)-9-amino-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4-a-diaza-benzocyclohepten-4-one in 3.5 ml of dichloromethane was added 0.030 mL (0.36 mmol) of 2-pyridine carboxaldehyde, 0.184 g (0.87 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. A recrystallization in isopropanol gives 0.042 g (35%) of pure product.

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. customA recrystallization in isopropanol

Sources & evidence

ORD record
ord-aa9e7657c8c645faa5a92a608a66cfc9
Source dataset
uspto-grants-2013_08
Patent number
US08501728B2

Reaction notes

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