Triethylamine → HCID 135559155, compound

HRID 372975Notes

Reaction equation

HRID 372975 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[NH:7])[CH3:2].Cl[C:14]1[C:19]([C:20](OCC)=[O:21])=[CH:18][N:17]=[C:16]([S:25][CH3:26])[N:15]=1.C(N(CC)CC)C>C(#N)C>[CH3:26][S:25][C:16]1[N:17]=[C:18]2[N:7]=[C:6]([C:5]3[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=3[O:3][CH2:1][CH3:2])[NH:8][C:20](=[O:21])[C:19]2=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 32510232-ethoxybenzamidine

Product 1

HCID 135559155HCID 135559155, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
2 °C

Procedure

2-Ethoxybenzamidine (from sodium, 0.08 g, in ethanol, 10 ml, and 2-ethoxybenzamidine hydrochloride, 0.70 g) was dissolved in acetonitrile (10 ml) and the resulting cooled (2° C.) solution was added to a cooled (2° C.) suspension of ethyl 4-chloro-2-methylthio-5-pyrimidine carboxylate (0.81 g) in acetonitrile (10 ml). The reaction mixture was stirred at 2° C. for one hour. Triethylamine (0.35 g) was added and the reaction mixture was stirred at ambient temperature for 21 hours to yield a white precipitate, 0.22 g, which was collected by filtration. The filtrate was reduced in volume under reduced pressure to yield a second crop of solid, 0.41 g. The products were combined and recrystallised from ethanol to yield the title compound, 0.30 g, m.p. 224.5°-225.5° C.

Workup

  1. additionwas added to
  2. temperaturea cooled
  3. stirringthe reaction mixture was stirred at ambient temperature for 21 hours
  4. customto yield a white precipitate, 0.22 g, which
  5. filtrationwas collected by filtration
  6. customto yield a second crop of solid, 0.41 g
  7. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-e6ba4ee620b547faba3bcc28d717bee2
Source dataset
uspto-grants-1992_11
Patent number
US05162316

Reaction notes

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