2-Nitroamino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone → 2-[2-(3-Bromo-2-pyridylmethylthio)ethylamino]-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone

HRID 127205Notes

Reaction equation

HRID 127205 reaction equation
[Br:1][C:2]1[C:3]([CH2:8][S:9][CH2:10][CH2:11][NH2:12])=[N:4][CH:5]=[CH:6][CH:7]=1.[N+](N[C:17]1[NH:22][C:21](=[O:23])[C:20]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[C:27]([O:31][CH3:32])[CH:26]=2)=[CH:19][N:18]=1)([O-])=O>C(O)C>[Br:1][C:2]1[C:3]([CH2:8][S:9][CH2:10][CH2:11][NH:12][C:17]2[NH:22][C:21](=[O:23])[C:20]([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([O:31][CH3:32])[CH:26]=3)=[CH:19][N:18]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 127838332-Nitroamino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidoneHCID 129515272-{[(3-Bromopyridin-2-yl)methyl]sulfanyl}ethan-1-amine

Product 1

HCID 127886752-[2-(3-Bromo-2-pyridylmethylthio)ethylamino]-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of 2-(3-bromo-2-pyridylmethylthio)ethylamine with 1.15 molar equivalents of 2-nitroamino-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone in refluxing ethanol for 18 hours gave 2-[2-(3-bromo-2-pyridylmethylthio)ethylamino]-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone m.p. 70-72° which was boiled under reflux in ethanol containing hydrogen chloride to give 2-[2-(3-bromo-2-pyridylmethylthio) ethylamino]-5-(2-hydroxy-4-pyridylmethyl)-4-pyrimidone trihydrochloride, m.p. 195-198.5°.

Sources & evidence

ORD record
ord-8a2f7444ab1f4d0a85dcc7436c55a7c4
Source dataset
uspto-grants-1981_03
Patent number
US04255428

Reaction notes

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