Triethyl orthoacetate → 7-cyclobutyl-3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

HRID 2368583Notes

Reaction equation

HRID 2368583 reaction equation
[CH:1]1([C:5]2[NH:13][C:12]3[C:11](=[O:14])[NH:10]/[C:9](=[N:15]\[NH2:16])/[N:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:7]=3[N:6]=2)[CH2:4][CH2:3][CH2:2]1.[C:22](OCC)(OCC)(OCC)[CH3:23]>>[CH:1]1([C:5]2[NH:13][C:12]3[C:11](=[O:14])[N:10]4[C:22]([CH3:23])=[N:16][N:15]=[C:9]4[N:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:7]=3[N:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 178446160HCID 178446160, compound

Product 1

HCID 250627897-cyclobutyl-3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-oneYield 10.6%

Conditions

Temperature
100 °C

Procedure

(2E)-8-cyclobutyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (100 mg, 0.0003 mol) was mixed with triethyl orthoacetate (10 mL, 0.05 mol) and then stirred at 100° C. overnight. After cooling to room temperature, the mixture was concentrated and purified by preparative LCMS to yield the desired product (10 mg, 9.2%). 1HNMR (300 MHz, CD3OD): δ 4.35 (m, 2H), 3.72 (m, 1H), 2.84 (s, 3H), 2.44 (m, 4H), 2.05 (m, 2H), 1.90 (m, 2H), 1.40 (m, 4H), 0.92 (m, 3H). LCMS calculated for C16H23N6O (M+H): 315.2. Found: 315.2.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-7eaf385554ca496e825f5202bc903a07
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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