Hydrochloric Acid → 2-Amino-alpha-cyano-alpha-(2-furanylmethyl)-1,6-dihydro-5-nitro6-oxo-4-pyrimidineacetic acid, ethyl ester

HRID 2372885Notes

Reaction equation

[H-].[Na+].[C:3]([CH:5]([CH2:10][C:11]1[O:12][CH:13]=[CH:14][CH:15]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:4].[NH2:16][C:17]1[NH:22][C:21](=[O:23])[C:20]([N+:24]([O-:26])=[O:25])=[C:19](Cl)[N:18]=1.Cl.[CH3:29]N(C=O)C>O>[NH2:16][C:17]1[NH:22][C:21](=[O:23])[C:20]([N+:24]([O-:26])=[O:25])=[C:19]([C:5]([C:3]#[N:4])([CH2:10][C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[C:6]([O:8][CH2:9][CH3:29])=[O:7])[N:18]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Sodium hydride (8.4 g, 60% suspension in oil, washed with hexane) is suspended in dry DMF (100 mL) under an atmosphere of dry N2 and a solution of methyl 2-cyano-3-(2-furanyl)propionate (U.S. Pat. No. 4,279,903) (37.6 g) in DMF (100 mL) is added dropwise. When the addition is complete, a clear red solution is formed. 2-Amino-6-chloro-5-nitro-4(3H)-pyrimidinone (recrystallized from methanol) (13.34 g) is added as a solid. The reaction mixture is heated at 100° C. for 1 h and at 65° C. overnight. The reaction mixture is cooled in an ice bath, acidified with 10% aq HCl and diluted with enough water to precipitate out the product 2-Amino-α-cyano-α-(2-furanylmethyl)-1,6-dihydro-5-nitro-6-oxo-4-pyrimidineacetic acid, ethyl ester. The product is collected by filtration and rinsed with water and ether (18.5 g). ##STR21##

Workup

additionWhen the addition
customa clear red solution is formed
temperatureThe reaction mixture is cooled in an ice bath
customto precipitate out the product 2-Amino-α-cyano-α-(2-furanylmethyl)-1,6-dihydro-5-nitro-6-oxo-4-pyrimidineacetic acid, ethyl ester
filtrationThe product is collected by filtration
washrinsed with water and ether (18.5 g)

Sources & evidence

ORD record: ord-9e907c1ed8924a6e976b70fa03dee448
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05101030

Reaction notes

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