Lithium hydroxide, monohydrate → HCID 178524135, compound

HRID 42311Notes

Reaction equation

HRID 42311 reaction equation
O.[OH-].[Li+].[O:4]([C:11]1[N:16]=[CH:15][C:14]([C:17]2[NH:21][N:20]=[C:19]([C:22]([O:24]CC)=[O:23])[CH:18]=2)=[CH:13][N:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C.O>[O:4]([C:11]1[N:12]=[CH:13][C:14]([C:17]2[NH:21][N:20]=[C:19]([C:22]([OH:24])=[O:23])[CH:18]=2)=[CH:15][N:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178468659HCID 178468659, compound

Product 1

HCID 178524135HCID 178524135, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution consisting of lithium hydroxide monohydrate (0.13 g, 3.0 mmol) dissolved in ethanol (10 mL)/water (5 mL) was added ethyl 5-(2-phenoxypyrimidin-5-yl)-1H-pyrazole-3-carboxylate (Example 54, 90 mg, 0.29 mmol) and the mixture was stirred at room temperature for 18 hours. Ethanol was removed under reduced pressure and the solution diluted with water and subsequently was acidified with acetic acid to precipitate product. The solid precipitate was filtered, washed with water, and dried under high vacuum to afford the title compound as a white solid (64 mg, 79% yield); Rf 0.15 with 2% methanol in dichloromethane; 1H-NMR (300 MHz; DMSO-d6) δ 9.12 (s, 2H), 7.49 (dd, 2H), 7.25-7.43 (m, 4H); MS (ESI−) m/z 281 (M−1); H-PGDS FPBA IC50: 5 μM.

Workup

  1. customEthanol was removed under reduced pressure
  2. additionthe solution diluted with water
  3. customto precipitate product
  4. filtrationThe solid precipitate was filtered
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-c112189030944d829972119b1a126268
Source dataset
uspto-grants-2013_09
Patent number
US08536185B2

Reaction notes

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