Methylamine → HCID 69219880, compound

HRID 901932Notes

Reaction equation

HRID 901932 reaction equation
[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[C:6]([C:17]2[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=2)=[N:5][C:4]=1SC)#[N:2].[CH3:27][NH2:28]>C(O)C>[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[C:6]([C:17]2[CH:18]=[CH:19][C:20]([S:23][CH3:24])=[CH:21][CH:22]=2)=[N:5][C:4]=1[NH:28][CH3:27])#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 9842817HCID 9842817, compound

Product 1

HCID 69219880HCID 69219880, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-cyano-1-(4-methylphenyl)-4-(methylthio)-2-[4-(methylthio)phenyl]-6-oxo-1,6-dihydropyrimidine (2 g, 5.3 mmol) (prepared according to the procedure disclosed in example 6) in ethanol (20 ml) with methylamine (0.33 g, 10.6 mmol) was refluxed for 2 hr. Then the reaction mass poured on to ice and the resulted solid filtered, washed thoroughly with water. The resulted solid purified by column chromatography using ethyl acetate and hexane mixture as eluent to yield title compound (0.55 g, yield 25.5%, mp 268-271° C., purity 97.34% by HPLC). 1H-NMR (CDCl3):δ 2.32 (s, 3H), 2.43 (s, 3H), 2.95 (d, 3H), 5.8 (s, 1H, D2O exchangeable), 6.95-6.97 (d, 3H), 7.02-7.04 (d, 1H), 7.11-7.13 (d, 1H), 7.22-7.26 (m, 3H). IR (KBr) cm−1: 3294, 2919, 2205 (—CN), 1666 (—C═O). MS m/z: 363.1 (M+).

Workup

  1. customprepared
  2. temperaturewas refluxed for 2 hr
  3. additionThen the reaction mass poured on to ice
  4. filtrationthe resulted solid filtered
  5. washwashed thoroughly with water
  6. customThe resulted solid purified by column chromatography

Sources & evidence

ORD record
ord-8a910f6440ad49e1b259fcd48f935e95
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Reaction notes

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