Hydrochloric Acid → HCID 68462226, compound

HRID 501191Notes

Reaction equation

HRID 501191 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:14]1[N:19]=[CH:18][C:17]([C:20]([O:22]C)=[O:21])=[CH:16][N:15]=1.[OH-].[Li+].Cl>C1COCC1.O>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:14]1[N:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58703314HCID 58703314, compound

Product 1

HCID 68462226HCID 68462226, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 8 (500 mg, mmol) in THF and water (10 mL, 1:1) was added lithium hydroxide (205 mg, mmol) at room temperature and the mixture was stirred for 4-5 hours. After completion, the reaction mixture was acidified using 1N hydrochloric acid. The mixture was extracted with EtOAc, washed with brine, the organics dried over sodium sulfate and concentrated to give 2-(1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)pyrimidine-5-carboxylic acid (400 mg, 83% yield).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialthe organics dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-edc5936308d243d9b7bf1a4e5278eef5
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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