Lithium Hydroxide → HCID 117778865, compound

HRID 2206622Notes

Reaction equation

HRID 2206622 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([C:13]([O:15]C)=[O:14])=[C:11]([CH3:17])[N:10]([C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])[C:8]=2[N:9]=1>O.O1CCCC1.CO>[Cl:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([C:13]([OH:15])=[O:14])=[C:11]([CH3:17])[N:10]([C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])[C:8]=2[N:9]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 89741701HCID 89741701, compound

Product 1

HCID 117778865HCID 117778865, compoundYield 75.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide anhydrate (882 mg, 21 mmol) in water (3 mL) was added to (R)-methyl 2-chloro-6-methyl-7-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (700 mg, 2.1 mmol) in tetrahydrofuran (5 mL) and methanol (10 mL) and the resultant mixture was stirred at room temperature for 12 hours. The mixture was evaporated, added with water (5 mL), acidified with aqueous hydrochloric acid (1M) to pH=2. The precipitate solid was filtered and dried to obtain (R)-2-chloro-6-methyl-7-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid as a white solid (500 mg, 75%). LRMS (M+H+) m/z: calcd 315.08. found 315.

Workup

  1. customThe mixture was evaporated
  2. additionadded with water (5 mL)
  3. filtrationThe precipitate solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-03d316e499cc4697927f0c3bb83d8e28
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

Loading…