Lithium Hydroxide → HCID 117778865, compound

HRID 1527109Notes

Reaction equation

HRID 1527109 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-b782c07905a24e56b226d240290c6c2f
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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