Potassium Hydroxide → 1256955-59-5

HRID 240998Notes

Reaction equation

HRID 240998 reaction equation
[CH3:1][CH:2]1[CH2:6][CH:5]([C:7]([O:9]C)=O)[C:4](=O)[CH2:3]1.S(O)(O)(=O)=O.[CH3:17][S:18][C:19](=[NH:21])[NH2:20].[OH-].[K+]>O>[CH3:1][CH:2]1[CH2:3][C:4]2[N:20]=[C:19]([S:18][CH3:17])[NH:21][C:7](=[O:9])[C:5]=2[CH2:6]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 14542963Methyl 4-methyl-2-oxocyclopentane-1-carboxylate

Product 1

HCID 1363315341256955-59-5Yield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 4-methyl-2-oxocyclopentanecarboxylate (0.42 g, 2.69 mmol), 2-methyl-2-thiopseudourea sulfate (1.10 g, 7.9 mmol) and potassium hydroxide (0.50 g, 8.9 mmol) in water (12 mL) was stirred at 25° C. for 30 minutes, and then heated to reflux for 4 hours. The reaction was cooled to 0° C. by adding ice and a precipitate was formed. The solid product was removed by filtration and the filter cake dried to give 6-methyl-2-(methylthio)-6,7-dihydro-3H-cyclopenta[d]pyrimidin-4(5H)-one (0.19 g, 43% yield) as a white solid. 1H NMR (400 MHz, d6-DMSO): 2.87 (m, 2H), 2.53 (s, 3H), 2.37 (m, 2H), 2.28 (s, 3H), 1.49 (m, 1H), 1.02 (d, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. additionby adding ice
  4. customa precipitate was formed
  5. customThe solid product was removed by filtration
  6. customthe filter cake dried

Sources & evidence

ORD record
ord-10719003aa4d4c89a6e7d321ff3bf4ff
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

Loading…