Picolinic acid → Ethyl 6,7,9,10-tetrahydro-4-oxo-10-[(2-pyridinylcarbonyl)amino]-2-(4-pyrimidinyl)pyrimido[1,2-d][1,4]diazepine-8(4H)-carboxylate

HRID 1890398Notes

Reaction equation

HRID 1890398 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].[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31](O)=[O:32].C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([NH:13][C:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=2)=[O:32])[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

8

Reactant 4

HCID 1018Picolinic acidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 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 44158890Ethyl 6,7,9,10-tetrahydro-4-oxo-10-[(2-pyridinylcarbonyl)amino]-2-(4-pyrimidinyl)pyrimido[1,2-d][1,4]diazepine-8(4H)-carboxylateYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.100 g (0.30 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 dissolved in 1.50 mL of dimethylformamide was added 0.041 g (0.33 mmol) of 2-pyridine carboxylic acid. To the resulting mixture was added 50 μL (0.33 mmol) of diethyl cyanophosphonate and 130 μL (0.91 mmol) of triethylamine at 0° C. The resulting mixture was stirred at room temperature for 15 hours. Water and ethyl acetate were added and the mixture was stirred. The resulting residue was filtered, washed with water, ethyl acetate and diethyl ether to afford 0.098 g (76%) of the pure product as a white powder.

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe resulting residue was filtered
  3. washwashed with water, ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-21ac145abd084f9f82e588d4ea063670
Source dataset
uspto-grants-2013_08
Patent number
US08507475B2

Reaction notes

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