Methylamine → HCID 16660232, compound

HRID 2356351Notes

Reaction equation

HRID 2356351 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]=1[S:25][CH3:26])#[N:2].[CH3:27][NH2:28]>CN(C=O)C.C(OC(=O)C)C.CCCCCC>[CH3:27][NH:28][C:1]1[C:3]([C:8]([NH:7][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[O:9])=[C:4]([S:25][CH3:26])[N:5]=[C:6]([C:17]2[CH:18]=[CH:19][C:20]([S:23][CH3:24])=[CH:21][CH:22]=2)[N:2]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 9842817HCID 9842817, compound

Product 1

HCID 16660232HCID 16660232, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution 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 our US patent 2004/0259891) in DMF was added methylamine (0.32 g, 10.5 mmol) under stirring. The solution was slowly warmed to 45° C., and maintained at this temperature for 1 hour. The completion of the reaction confirmed by TLC using ethylacetate:hexane (1:1) as a solvent system. The resulted reaction mass was poured onto ice and filtered, the crude solid thus obtained was purified by column chromatography using ethylacetate:hexane to give the title compound, 0.8 g, yield 37%, purity 99.5% by HPLC, m.p.: 228-230° C. 1H-NMR (CDCl3) δ (ppm): 2.35 (s, 3H), 2.54 (s, 3H), 2.73 (s, 3H), 3.1-3.13 (d, 3H), 7.17-7.20 (d, 2H), 7.30-7.32 (d, 2H), 7.48-7.5 (d, 2H), 7.9 (bs, 1H), 8.35 (bs, 1H), and 8.4-8.42 (d, 2H). IR (KBr) cm−1: 3358, 3270, and 1625. MS m/z: 411.1 (M++1).

Workup

  1. temperaturemaintained at this temperature for 1 hour
  2. customThe resulted reaction mass
  3. additionwas poured onto ice
  4. filtrationfiltered
  5. customthe crude solid thus obtained
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-3510c8f7312d4e46b7f63f45142b7673
Source dataset
uspto-grants-2010_07
Patent number
US07759350B2

Reaction notes

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