4-Hydroxybenzoic Acid → 3-Butyl-8-chloro-1-{4-[5-(4-hydroxyphenyl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

HRID 1097691Notes

Reaction equation

HRID 1097691 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=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:6]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=3)[O:8][N:33]=2)[C:16]1=[O:35])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 178506472HCID 178506472, compound

Product 1

HCID 1361587903-Butyl-8-chloro-1-{4-[5-(4-hydroxyphenyl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dioneYield 4.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

4-Hydroxybenzoic acid (35 mg, 0.25 mmol) and CDl (45 mg, 0.28 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 (100 mg, 0.28 mmol) was added and the mixture was stirred at 90° C. for 16 h. The mixture was purified by MDAP to give the title compound as a white solid (5 mg, 4%).

Workup

  1. additionwas added
  2. customThe mixture was purified by MDAP

Sources & evidence

ORD record
ord-db8bc73487f34f3399fd3c0f9840952f
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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