Triethylamine → 7-Methylthio-2-(2-isobutoxyphenyl)-4-oxo-3,4-dihydropyrimido[4.5-d]pyrimidine

HRID 372977Notes

Reaction equation

HRID 372977 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.C(N(CC)CC)C.Cl.[CH2:23]([O:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH2:32])=[NH:31])[CH:24]([CH3:26])[CH3:25]>C(#N)C>[CH3:14][S:13][C:4]1[N:3]=[C:2]2[N:31]=[C:30]([C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[O:27][CH2:23][CH:24]([CH3:26])[CH3:25])[NH:32][C:8](=[O:10])[C:7]2=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 224623702-Isobutoxybenzamidine hydrochloride

Product 1

HCID 1355591567-Methylthio-2-(2-isobutoxyphenyl)-4-oxo-3,4-dihydropyrimido[4.5-d]pyrimidineYield 21.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

Ethyl 4-chloro-2-methylthio-5-pyrimidine carboxylate (1.50 g) followed by triethylamine (0.65 g) was added to a stirred mixture of 2-isobutoxybenzamidine hydrochloride (1.46 g) and triethylamine (0.65 g) in acetonitrile (150 ml). The reaction mixture was stirred at 5° C. for 15 minutes and then at ambient temperature for 3 days. A solid (0.55 g) was collected by filtration and the filtrate was reduced in volume to yield a second crop of solid (0.47 g). The solids were combined and recrystallised from ethanol to yield the title compound, 0.57 g, m.p. 185°-186° C.

Workup

  1. waitat ambient temperature for 3 days
  2. filtrationA solid (0.55 g) was collected by filtration

Sources & evidence

ORD record
ord-70b69d84fe414f10b8179a4d8d73759e
Source dataset
uspto-grants-1992_11
Patent number
US05162316

Reaction notes

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