Tert-Butylamine → 1-(3-tert-butylamino-2-hydroxy-1-propyl)-6-(3,4-dimethoxyphenyl)-3-methyl-2,4(1H,3H)pyrimidinedione

HRID 65155Notes

Reaction equation

HRID 65155 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH2:17][CH:18]3[O:20][CH2:19]3)[C:15](=[O:21])[N:14]([CH3:22])[C:13](=[O:23])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:24]([NH2:28])([CH3:27])([CH3:26])[CH3:25]>>[C:24]([NH:28][CH2:19][CH:18]([OH:20])[CH2:17][N:16]1[C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:12][C:13](=[O:23])[N:14]([CH3:22])[C:15]1=[O:21])([CH3:27])([CH3:26])[CH3:25]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 140964716-(3,4-dimethoxyphenyl)-1-(2,3-epoxypropyl)-3-methyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 212432321-(3-tert-butylamino-2-hydroxy-1-propyl)-6-(3,4-dimethoxyphenyl)-3-methyl-2,4(1H,3H)pyrimidinedione

Procedure

To a solution of 6-(3,4-dimethoxyphenyl)-1-(2,3-epoxypropyl)-3-methyl-2,4(1H,3H)-pyrimidinedione (0.6 g) in ehtanol (20 ml) was added tert-butylamine (2 ml). The mixture was refluxed for 2.5 hours and evaporated in vacuo. The resulting syrup was triturated in a mixture of diethyl ether and diisopropyl ether to give 1-(3-tert-butylamino-2-hydroxy-1-propyl)-6-(3,4-dimethoxyphenyl)-3-methyl-2,4(1H,3H)pyrimidinedione (0.66 g).

Workup

  1. temperatureThe mixture was refluxed for 2.5 hours
  2. customevaporated in vacuo
  3. customThe resulting syrup was triturated in a mixture of diethyl ether and diisopropyl ether

Sources & evidence

ORD record
ord-a24a2751e30a4caa92c7ef2c753bad59
Source dataset
uspto-grants-1986_09
Patent number
US04612376

Reaction notes

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