Ethylorthoformate → 4-pentyl-1,4-dihydro-9H-[1,2,4]triazolo[1,5-a]purin-9-one

HRID 2368614Notes

Reaction equation

HRID 2368614 reaction equation
[NH2:1][N:2]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:3]1=[NH:17].[CH:18]([O-])([O-])OCC>>[CH2:12]([N:4]1[C:5]2[N:6]=[CH:7][NH:8][C:9]=2[C:10](=[O:11])[N:2]2[N:1]=[CH:18][N:17]=[C:3]12)[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 53630039EthylorthoformateHCID 576003161-amino-2-imino-3-pentyl-1,2,3,7-tetrahydro-6H-purin-6-one

Product 1

HCID 576002184-pentyl-1,4-dihydro-9H-[1,2,4]triazolo[1,5-a]purin-9-oneYield 20.3%

Conditions

Temperature
100 °C

Procedure

The mixture of 1-amino-2-imino-3-pentyl-1,2,3,7-tetrahydro-6H-purin-6-one (0.10 g, 0.4 mmol) and ethyl orthoformate (5 mL, 30 mmol) was stirred at 100° C. for 6 hours. The reaction mixture was concentrated and purified by preparative LCMS to yield the desired product (20 mg, 20%). LCMS calculated for C11H15N6O (M+H): 247.1. Found: 247.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-3356b5a6e724474cae98ee8f940e459f
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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