2-{[(3-Bromopyridin-2-yl)methyl]sulfanyl}ethan-1-amine → 2-[2-(3-Bromo-2-pyridylmethylthio)ethylamino]-5-(4-pyridylmethyl)-4-pyrimidone

HRID 1855838Notes

Reaction equation

HRID 1855838 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[C:9](=[O:16])[NH:10][C:11](SC)=[N:12][CH:13]=2)=[CH:3][CH:2]=1.[Br:17][C:18]1[C:19]([CH2:24][S:25][CH2:26][CH2:27][NH2:28])=[N:20][CH:21]=[CH:22][CH:23]=1>>[Br:17][C:18]1[C:19]([CH2:24][S:25][CH2:26][CH2:27][NH:28][C:11]2[NH:10][C:9](=[O:16])[C:8]([CH2:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[CH:13][N:12]=2)=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 129515272-{[(3-Bromopyridin-2-yl)methyl]sulfanyl}ethan-1-amineHCID 143385852-(Methylsulfanyl)-5-[(pyridin-4-yl)methyl]pyrimidin-4(3H)-one

Product 1

HCID 30788512-[2-(3-Bromo-2-pyridylmethylthio)ethylamino]-5-(4-pyridylmethyl)-4-pyrimidone

Procedure

5-(4-Pyridylmethyl)-2-methylthio-4-pyrimidone (1.1 g) was reacted with 2-(3-bromo-2-pyridylmethylthio)ethylamine (1.15 g) according to the procedure of Example 2. The reaction mixture was triturated under hot water to give 2-[2-(3-bromo-2-pyridylmethylthio)ethylamino]-5-(4-pyridylmethyl)-4-pyrimidone. This product was acidified with dilute ethanolic hydrogen chloride, evaporated to dryness and the residue recrystallised from ethanol to give the title compound m.p. 211°-215° (decomp). (Found: C, 42.65; H, 3.9; N, 13.9; S, 6.3; C18H18Br N5OS.2HCl requires: C, 42.8; H, 4.0; N, 13.9; S, 6.35%)

Workup

  1. customThe reaction mixture was triturated under hot water

Sources & evidence

ORD record
ord-addfe4b763bf446c996e642fc0c38ac2
Source dataset
uspto-grants-1980_08
Patent number
US04216318

Reaction notes

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