Methanol → HCID 178489277, compound

HRID 2370231Notes

Reaction equation

HRID 2370231 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[CH2:17][CH2:16][CH:15]([C:18](OC)=[O:19])[C:14]1=O.CO>O>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[C:14]2[N:1]=[C:2]([OH:3])[N:4]=[C:18]([OH:19])[C:15]=2[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1176UreaHCID 58075770HCID 58075770, compound

Product 1

HCID 178489277HCID 178489277, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a melt of urea (6.07 g, 101 mmol) (bath temp 150° C.) was added methyl 3-(2-methoxyphenyl)-2-oxocyclopentanecarboxylate (5.3 g, 20.21 mmol) dropwise. After stirring overnight, the reaction was cooled to rt. Added MeOH (30 ml), and broke up the solid mass with a spatula and stirred for 1 h. Added water (600 ml), and stirred for 3 hr. The mixture was added to a Buchner funnel, and washed with water. Dried overnight in the vacuum oven (45° C.) to obtain 7-(2-methoxyphenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol (4.03 g, 15.60 mmol, 77% yield) as a tan solid. LC-MS (M+H)+=259.1.

Workup

  1. stirringstirred for 1 h
  2. additionThe mixture was added to a Buchner funnel
  3. washwashed with water
  4. customDried overnight in the vacuum oven (45° C.)

Sources & evidence

ORD record
ord-15a87a5d5d284b3eba76fbf6f6d9ce4e
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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