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

HRID 464610Notes

Reaction equation

HRID 464610 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-a19745e9fd3e418d8095cdd4c94ba264
Source dataset
uspto-grants-1985_10
Patent number
US04548818

Reaction notes

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