p-Toluenesulfonic acid monohydrate → HCID 178485563, compound

HRID 334149Notes

Reaction equation

HRID 334149 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:6](C2CCCCO2)[C:7]2[C:12]([N:13]=1)=[C:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[N:10]=[C:9]([Cl:20])[N:8]=2)=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O.C(=O)(O)[O-].[Na+]>[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([N:13]=1)=[C:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[N:10]=[C:9]([Cl:20])[N:8]=2)=[O:4]

Participants

6

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86667366HCID 86667366, compound

Product 1

HCID 178485563HCID 178485563, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-Chloro-6-morpholin-4-yl-9-(tetrahydro-pyran-2-yl)-9H-purine-8-carboxylic acid methylamide (104 mg, 0.27 mmol) was suspended in methanol (6 mL) and p-toluenesulfonic acid monohydrate (10 mg, 0.05 mmol) was added. The mixture was stirred at room temperature for 68 h, then diluted with water and neutralized with aqueous sodium bicarbonate. The solid precipitate was filtered off and dried at 50° C. under vacuum to give 2-chloro-6-morpholin-4-yl-9H-purine-8-carboxylic acid methylamide (56 mg, 70%). LCMS RT=2.43, [M+H]+=297/299

Workup

  1. filtrationThe solid precipitate was filtered off
  2. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-1492cf5858164a5db651a26bd2467990
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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