HCID 178450806, compound → HCID 178524866, compound

HRID 2169314Notes

Reaction equation

HRID 2169314 reaction equation
C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C>O1CCCC1.O>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:25][CH2:26][CH2:27][CH2:28]2)=[N:11][C:12]=1[OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 178450806HCID 178450806, compound

Product 1

HCID 178524866HCID 178524866, compoundYield 55.44%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (282) (1.6 g. 3.48 mmol) in a mixture of tetrahydrofuran:water (2:1) (90 mL), was added lithium-hydroxide monohydrate (2.9 g, 69.57 mmol) and the reaction mixture was refluxed for 18 h. After completion of the reaction, all volatiles were evaporated, added water (30 mL) and washed with ethyl acetate (2×20 mL) to remove non acidic impurities. The separated aqueous part was acidified with 1N HCl to reach a pH of about 5 to 6. The acidified aqueous part was extracted with ethyl acetate (4×50 mL), dried and concentrated to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (283) (780 mg, 55.44%) as a white solid.

Workup

  1. additionwas added lithium-hydroxide monohydrate (2.9 g, 69.57 mmol)
  2. temperaturethe reaction mixture was refluxed for 18 h
  3. customAfter completion of the reaction
  4. customall volatiles were evaporated
  5. additionadded water (30 mL)
  6. washwashed with ethyl acetate (2×20 mL)
  7. customto remove non acidic impurities
  8. extractionThe acidified aqueous part was extracted with ethyl acetate (4×50 mL)
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e544742fce6c47179f410d7d7c59ea15
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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