Hydrochloric Acid → 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylic acid

HRID 2175927Notes

Reaction equation

HRID 2175927 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:12]([C:13]([O:15]C)=[O:14])[CH2:11][CH2:10][C:8]=2[N:9]=1.Cl>CO>[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:12]([C:13]([OH:15])=[O:14])[CH2:11][CH2:10][C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86727113methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate

Product 1

HCID 838618122-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (13.0 mL, 13.0 mmol) was added to a solution of methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate (1.10 g, 5.69 mmol) in methanol (21 mL). The resulting mixture was stirred at RT for 1.5 hours. Hydrochloric acid (13 mL, 13.00 mmol) was added. The solvent was evaporated. The residue was purified by chromatography on silica (24 g cartridge) eluting with CH2Cl2:MeOH 95:5 (150 mL) and CH2Cl2:MeOH:AcOH 90:10:1 to afford the title compound.

Workup

  1. customThe solvent was evaporated
  2. customThe residue was purified by chromatography on silica (24 g cartridge)
  3. washeluting with CH2Cl2:MeOH 95:5 (150 mL) and CH2Cl2:MeOH:AcOH 90:10:1

Sources & evidence

ORD record
ord-1b8bf926f96d474dab99129277f98c06
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

Loading…