Ammonium Hydroxide → 2,4-Diamino-5-(6,7-dimethoxy-2,3-dimethyl-4-benzofuranylmethyl)pyrimidine

HRID 280698Notes

Reaction equation

HRID 280698 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH:17]([CH3:21])[C:18](=O)[CH3:19])[C:13]([O:22][CH3:23])=[C:12]([O:24][CH3:25])[CH:11]=2)=[CH:4][N:3]=1.[OH-].[NH4+]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[C:15]3[C:18]([CH3:19])=[C:17]([CH3:21])[O:16][C:14]=3[C:13]([O:22][CH3:23])=[C:12]([O:24][CH3:25])[CH:11]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 233211222,4-Diamino-5-(3,4-dimethoxy-5-(1-methyl-2-oxopropoxy)benzyl)pyrimidine

Product 1

HCID 233211292,4-Diamino-5-(6,7-dimethoxy-2,3-dimethyl-4-benzofuranylmethyl)pyrimidineYield 79.2%

Procedure

A mixture of 0.70 g (0.002 mole) of 2,4-diamino-5-(3,4-dimethoxy-5-(1-methyl-2oxopropoxy)benzyl)pyrimidine in 11 g of polyphosphoric acid was stirred and heated on a steam bath for 20 minutes then poured onto 100 g of ice. The resulting mixture was basified with concentrated ammonium hydroxide, then extracted with methylene chloride (100 mL). The extract was washed with water (150 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (0.52 g, 78%). Recrystallization from absolute ethanol gave an analytical sample; mp>249° dec. Anal. Calcd for C17H20N4O3 : C, 62.18, H, 6.14; N, 17.06. Found: C, 62.01; H, 6.17, N, 17.01.

Workup

  1. temperatureheated on a steam bath for 20 minutes
  2. extractionextracted with methylene chloride (100 mL)
  3. washThe extract was washed with water (150 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b1d6dfb4c1b434ab9aebbb93b3ca966
Source dataset
uspto-grants-1986_05
Patent number
US04590271

Reaction notes

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