HCID 67459131, compound → HCID 67460719, compound

HRID 1470317Notes

Reaction equation

HRID 1470317 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH2:15][C:16]([O:18]CC)=[O:17])=[CH:13][N:12]=[C:11]([N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][N:12]=[C:11]([N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 67459131HCID 67459131, compound

Product 1

HCID 67460719HCID 67460719, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidin-5-yl)acetate, 12-b, (90 mg, 0.27 mmol) in TRF (6 ml) was added LiOH monohydrate (19 mg, 0.8 mmol) in H2O (3 ml). The mixture was stirred at room temperature for 3 hours. The mixture was concentrated under vacuum and the remaining aqueous solution was extracted with ethyl acetate (5 ml). The separated aqueous phase was adjusted to pH=2 with Conc. HCl. The solid crashed out and was filtered to give compound 12-c (40 mg, 48.5%). 1HNMR (DMSO-d6, 300 MHz): δ 12.56 (s, 1H), 8.66 (s, 1H), 8.47 (s, 1H), 7.84 (s, 1H), 7.32-7.52 (M, 5H), 6.59 (s, 1H), 5.57 (S, 2H), 3.61 (s, 2H). (M+H)+=311.1.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. extractionthe remaining aqueous solution was extracted with ethyl acetate (5 ml)
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-af6ea6604c66412083bd6084d151e111
Source dataset
uspto-grants-2015_04
Patent number
US09006433B2

Reaction notes

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