5-Hydroxypyridine-2-carboxylic acid → 3-Butyl-8-chloro-1-{4-[5-(5-hydroxy-2-pyridinyl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

HRID 1097694Notes

Reaction equation

HRID 1097694 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[CH2:11]([N:15]1[C:23]2[N:22]=[C:21]([Cl:24])[NH:20][C:19]=2[C:18](=[O:25])[N:17]([CH2:26][CH2:27][CH2:28][CH2:29]/[C:30](=[N:33]/[H])/[NH:31]O)[C:16]1=[O:35])[CH2:12][CH2:13][CH3:14]>CS(C)=O>[CH2:11]([N:15]1[C:23]2[N:22]=[C:21]([Cl:24])[NH:20][C:19]=2[C:18](=[O:25])[N:17]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[N:31]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][N:6]=3)[O:10][N:33]=2)[C:16]1=[O:35])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 2687405-Hydroxypyridine-2-carboxylic acidHCID 178506472HCID 178506472, compound

Product 1

HCID 1361588003-Butyl-8-chloro-1-{4-[5-(5-hydroxy-2-pyridinyl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dioneYield 24.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

5-Hydroxy-2-pyridinecarboxylic acid (24 mg, 0.17 mmol) and CDl (31 mg, 0.19 mmol) were stirred in anhydrous DMSO (0.9 ml) at rt for 1 h. (1Z)-5-(3-Butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxypentanimidamide (68 mg, 0.19 mmol) was added and the mixture was stirred at 90° C. for 16 h. The mixture was purified by MDAP and the product fractions concentrated to give the title compound as a white solid (19 mg, 24%).

Workup

  1. additionwas added
  2. customThe mixture was purified by MDAP
  3. concentrationthe product fractions concentrated

Sources & evidence

ORD record
ord-f77cc7c8d48744278faf0b7fdd4ce6d3
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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