5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonic acid {4-[1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide → 1,3-Dimethyl-1H-pyrazole-4-sulfonic acid [4-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-amide

HRID 858053Notes

Reaction equation

HRID 858053 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[NH:8][C:7]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][S:20]([C:23]4[C:24]([CH3:30])=[N:25][N:26]([CH3:29])[C:27]=4Cl)(=[O:22])=[O:21])=[CH:15][CH:14]=3)=[N:6][C:5]=2[N:4]([CH3:31])[C:3]1=[O:32]>CO>[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[NH:8][C:7]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][S:20]([C:23]4[C:24]([CH3:30])=[N:25][N:26]([CH3:29])[CH:27]=4)(=[O:22])=[O:21])=[CH:15][CH:14]=3)=[N:6][C:5]=2[N:4]([CH3:31])[C:3]1=[O:32]

Participants

3

Reactant 1

HCID 103449845-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonic acid {4-[1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide

Product 1

HCID 103433561,3-Dimethyl-1H-pyrazole-4-sulfonic acid [4-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloro-1,3-dimethyl-1H-pyrazole-4-sulfonic acid {4-[1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide (0.082 mmol) was dissolved in methanol (70 mL) and dichloromethane (10 mL) and the reaction vessel flushed with argon before adding 10% palladium on carbon (100 mg). The reaction vessel was charged with hydrogen gas at 50 psi pressure and shaken for 24 hrs. Additional 10% palladium on carbon (50 mg) was added and hydrogenolysis continued at 50 psi pressure of hydrogen gas for an additional 24 hrs. At this time no starting material remained. The reaction mixture was filtered through celite and concentrated in vacuo. The crude product was purified by chromatography using silica eluted with 10% v/v methanol in chloroform to give after concentration in vacuo 1,3-dimethyl-1H-pyrazole-4-sulfonic acid [4-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-amide as a colorless solid (38%); EI-HRMS m/e calculated for C19H21N7O4S (M+) 443.1376, found 443.1364.

Workup

  1. customdichloromethane (10 mL) and the reaction vessel flushed with argon
  2. additionbefore adding 10% palladium on carbon (100 mg)
  3. additionThe reaction vessel was charged with hydrogen gas at 50 psi pressure
  4. additionAdditional 10% palladium on carbon (50 mg) was added
  5. waithydrogenolysis continued at 50 psi pressure of hydrogen gas for an additional 24 hrs
  6. filtrationThe reaction mixture was filtered through celite and
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography
  9. washeluted with 10% v/v methanol in chloroform
  10. customto give
  11. concentrationafter concentration in vacuo 1,3-dimethyl-1H-pyrazole-4-sulfonic acid [4-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-amide as a colorless solid (38%)

Sources & evidence

ORD record
ord-9d7af791dca94db88a4bbb77580ad44f
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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