Diethyl Ether → 6-Hydroxy-8-methyl-3-(2-methylpropyl)-3,9-dihydro-2H-purin-2-one

HRID 236305Notes

Reaction equation

HRID 236305 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[NH:4][C:5](=[O:13])[N:6]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:7]=1[NH2:8].C(Cl)(Cl)Cl.[CH3:19][CH2:20]OCC>C(O)(=O)C>[CH3:19][C:20]1[NH:1][C:2]2[C:3](=[O:14])[NH:4][C:5](=[O:13])[N:6]([CH2:9][CH:10]([CH3:11])[CH3:12])[C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 105841095,6-Diamino-1-(2-methylpropyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 30590036-Hydroxy-8-methyl-3-(2-methylpropyl)-3,9-dihydro-2H-purin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10 g of 5,6-diamino-1-(2-methylpropyl)-2,4-(1H,3H)-pyrimidine dione was refluxed in 50 ml of acetic acid for 1 hour. 30 ml of chloroform was added and ether was then added slowly. The received crystals were filtered off. Yield 10.8 g. The amide was refluxed in 30 ml of 2N NaOH for 1 hour and then neutralized with 5N HCl. The crystals were filtered off and recrystallized from 50 ml of acetic acid. Yield 3.3 g. NMR (see Table I).

Workup

  1. filtrationThe received crystals were filtered off
  2. temperatureThe amide was refluxed in 30 ml of 2N NaOH for 1 hour
  3. filtrationThe crystals were filtered off
  4. customrecrystallized from 50 ml of acetic acid

Sources & evidence

ORD record
ord-5b8ad565345e41798ec6deb220cdcd93
Source dataset
uspto-grants-1987_02
Patent number
US04644001

Reaction notes

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