Methylamine → HCID 69220139, compound

HRID 901933Notes

Reaction equation

HRID 901933 reaction equation
[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[CH:11]=2)[C:6]([C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=2)=[N:5][C:4]=1SC)#[N:2].[CH3:28][NH2:29]>C(O)C>[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[CH:11]=2)[C:6]([C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=2)=[N:5][C:4]=1[NH:29][CH3:28])#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68454150HCID 68454150, compound

Product 1

HCID 69220139HCID 69220139, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-cyano-1-(3,4-dimethylphenyl)-4-(methylthio)-2-[4-(methylthio)phenyl]-6-oxo-1,6-dihydropyrimidine (1 g, 2.5 mmol) (prepared according to example 10) in ethanol (10 ml) with methylamine (0.16 g, 5 mmol) was refluxed for 3 hr. Then the reaction mass poured on to ice and the resulted solid filtered, washed thoroughly with water. The solid thus obtained was purified by column chromatography using ethyl acetate and hexane mixture as eluent to yield title compound (0.36 g, yield 38%, mp 199-205° C., purity 98.72% by HPLC). 1H-NMR (CDCl3):δ 2.19 (s, 3H), 2.22 (s, 3H), 2.44 (s, 3H), 3.17-3.18 (d, 3H), 5.73 (s, 1H, D2O exchangeable) 6.75-6.77 (d, 2H), 6.90 (s, 1H), 7.02-7.06 (m, 3H), 7.24-7.26 (d, 1H). IR (KBr) cm−1: 3280, 2920, 2207 (—CN), 1661 (—C═O). MS m/z:377.2 (M+).

Workup

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

Sources & evidence

ORD record
ord-484d925517094e6fb2258e6fe2dc9175
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Reaction notes

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