Hydrochloric Acid → 4-[(5-Methoxy-2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid

HRID 1049853Notes

Reaction equation

HRID 1049853 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:13][C:14]2[C:15]3[CH:22]=[C:21]([C:23]([O:25]CC)=[O:24])[NH:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:5][C:6]2[S:10][C:9](=[O:11])[NH:8][C:7]=2[CH:12]=1.[OH-].[Li+].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([NH:13][C:14]2[C:15]3[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[NH:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:5][C:6]2[S:10][C:9](=[O:11])[NH:8][C:7]=2[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 73442308Ethyl 4-[(5-methoxy-2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 734423094-[(5-Methoxy-2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acidYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 15 mg (39 μmol) ethyl 4-[(5-methoxy-2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate (prepared according to example 25), 234 μL aqueous lithium hydroxide (1 molar), and 1.0 mL tetrahydrofuran was stirred at room temperature overnight. The mixture was then acidified by addition of aqueous hydrochloric acid (4 N). The precipitate was filtered, washed with water and diethyl ether and dried to give 10.1 mg (69%) of the title compound.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water and diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-4a6689e7b0dc4271aea84f89869ea92d
Source dataset
uspto-grants-2016_07
Patent number
US09382255B2

Reaction notes

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