Lithium hydroxide, monohydrate → 4-[5Chloro-2-(1-hydroxymethylpropylamino)-pyrimidin-4-yl]-benzoic acid

HRID 968689Notes

Reaction equation

HRID 968689 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([Cl:16])=[CH:14][N:13]=[C:12]([NH:17][CH:18]([CH2:21][OH:22])[CH2:19][CH3:20])[N:11]=2)=[CH:6][CH:5]=1.O.[OH-].[Li+]>C1COCC1.O.Cl>[Cl:16][C:15]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:23])=[O:2])=[CH:5][CH:6]=2)=[N:11][C:12]([NH:17][CH:18]([CH2:21][OH:22])[CH2:19][CH3:20])=[N:13][CH:14]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 694214084-[5-Chloro-2-(1-hydroxymethylpropylamino)-pyrimidin-4-yl]-benzoic acid methyl ester

Product 1

HCID 694209224-[5Chloro-2-(1-hydroxymethylpropylamino)-pyrimidin-4-yl]-benzoic acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[5-Chloro-2-(1-hydroxymethylpropylamino)-pyrimidin-4-yl]-benzoic acid methyl ester (68 mg, 0.20 mmol) was dissolved in 4 mL THF. To this solution 41 mg of lithium hydroxide monohydrate in 2 mL water was added and the reaction mixture stirred for 3 days. The reaction mixture was diluted with 1N HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to afford 4-[5chloro-2-(1-hydroxymethylpropylamino)-pyrimidin-4-yl]-benzoic acid as a yellow solid, 64 mg, 0.20 mmol. LCMS ES+=322.1.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2d5c01848b9a41d2aad349e3e86fa366
Source dataset
uspto-grants-2007_12
Patent number
US07304071B2

Reaction notes

Loading…