Ethyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate → 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid

HRID 1525236Notes

Reaction equation

HRID 1525236 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][N:12]=[C:11]([N:20]2[CH:24]=[CH:23][CH:22]=[N:21]2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.O>[CH2:1]([O:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[C:11]([N:20]2[CH:24]=[CH:23][CH:22]=[N:21]2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67460482Ethyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate2×

Product 1

HCID 674594834-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acidYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate, 11-b, (150 g, 0.46 mol) in THF (1.5 L) was treated with LiOH monohydrate (58 g, 1.39 mol) in water (60 ml) at room temperature for 3 hours. The mixture was concentrated under vacuum and diluted with water (200 ml) followed by extraction with ethyl acetate. The aqueous layer was acidified to pH=2 with 10% HCl and solid crashed out from the solution which was then filtered and washed with water to afford the product, 11-c, (40 g, 29%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additiondiluted with water (200 ml)
  3. extractionfollowed by extraction with ethyl acetate
  4. filtrationwas then filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-886592c3f49c487bbf23d818bb190485
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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