Lithium Hydroxide → HCID 16665944, compound

HRID 219674Notes

Reaction equation

HRID 219674 reaction equation
C[O:2][C:3]([C:5]1[NH:9][C:8]2[CH:10]=[C:11]([NH:14][C:15]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:21][CH:22]=3)=[O:16])[CH:12]=[CH:13][C:7]=2[N:6]=1)=[O:4].[Li+].[OH-]>CO.O.O1CCCC1>[C:23]1([C:20]2[N:19]=[CH:18][C:17]([C:15]([NH:14][C:11]3[CH:12]=[CH:13][C:7]4[N:6]=[C:5]([C:3]([OH:4])=[O:2])[NH:9][C:8]=4[CH:10]=3)=[O:16])=[CH:22][N:21]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 16665943HCID 16665943, compound

Product 1

HCID 16665944HCID 16665944, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 6-[(2-phenyl-pyrimidin-5-carbonyl)-amino]-1H-benzoimidazole-2-carboxylic acid methyl ester (0.44 mmol) and LiOH (4.40 mmol) in MeOH/water/tetrahydrofuran (1:1:1, 60 mL) is stirred at room temperature overnight. MeOH and THF are evaporated in vacuo and the aqueous mixture is acidified with 5% HCl to pH ˜2. The resulting precipitate is filtered, washed with water (10 mL) and dried to give 6-[(2-phenyl-pyrimidin-5-carbonyl)-amino]-1H-benzoimidazole-2-carboxylic acid as a solid (115 mg). MS: 360 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 7.52-7.70 (m, 5H), 8.30 (s, H), 8.48 (m, 3H), 9.28 (S, H), 9.38 (s, 2H), 10.73 (s, N—H).

Workup

  1. customMeOH and THF are evaporated in vacuo
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with water (10 mL)
  4. customdried

Sources & evidence

ORD record
ord-9a749bfd25d3407da7d4ea892daaf6d4
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

Loading…