Sodium Hydroxide → HCID 59362896, compound

HRID 1668812Notes

Reaction equation

HRID 1668812 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]3[C:24]4[CH2:25][CH2:26][CH2:27][C:23]=4[N:22]=[C:21]([CH:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[N:20]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6]>O.CO>[CH:28]1([C:21]2[N:20]=[C:19]([NH:18][C:15]3[CH:14]=[CH:13][C:12]([C:7]4([C:5]([OH:6])=[O:4])[CH2:11][CH2:10][CH2:9][CH2:8]4)=[CH:17][CH:16]=3)[C:24]3[CH2:25][CH2:26][CH2:27][C:23]=3[N:22]=2)[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59362947HCID 59362947, compound

Product 1

HCID 59362896HCID 59362896, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of sodium hydroxide (4.14 g, 100 mmol) in water (100 mL) was added to a solution of 1-[4-(2-cyclopentyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclopentanecarboxylic acid methyl ester (7.0 g, 17.2 mmol) in MeOH (100 mL) and the mixture was heated at 90° C. for 8 hours. After evaporation of MeOH under reduced pressure, the mixture was cooled to a temperature in the range of 15° C. to 40° C., and acidified with hydrochloric acid to adjust pH to 3-4. The precipitate formed after standing at a temperature in the range of 15° C. to 40° C. was filtered and washed several times with water, and dried under vacuum. The solid was recrystallized from MeOH to afford the title compound as a white powder (6.3 g, 94% yield).

Workup

  1. customAfter evaporation of MeOH under reduced pressure
  2. temperaturethe mixture was cooled to a temperature in the range of 15° C. to 40° C.
  3. customThe precipitate formed
  4. customafter standing at a temperature in the range of 15° C. to 40° C.
  5. filtrationwas filtered
  6. washwashed several times with water
  7. customdried under vacuum
  8. customThe solid was recrystallized from MeOH

Sources & evidence

ORD record
ord-1a27c998b09e4587a485871d2b7b72e5
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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