Isoamylamine → HCID 20924707, compound

HRID 1449135Notes

Reaction equation

HRID 1449135 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[C:7]([C:9]1[C:10]([CH3:19])=[N:11][O:12][C:13]=1[N:14]=[CH:15]OCC)#[N:8].[O-]CC.[Na+].[Na]>C(O)C.O>[CH3:19][C:10]1[C:9]2[C:13](=[N:14][CH:15]=[N:8][C:7]=2[NH:5][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1])[O:12][N:11]=1

Participants

7

Reactant 4

HCID 7894IsoamylamineHCID 305619HCID 305619, compoundHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 20924707HCID 20924707, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

3-Methylbutylamine (1.74 g) was added dropwise to a solution of 4-cyano-5-ethoxymethyleneamino-3-methylisoxazole (3.6 g, prepared as described by E C Taylor and E E Garcia, J. Org. Chem., 1964, 29, 2116) in ethanol (30 ml). The mixture was stirred for ten minutes* at room temperature, treated with a solution of sodium ethoxide** (from 0.46 g sodium) in ethanol (10 ml) and refluxed*** for four hours. It was then cooled and diluted with water. The precipitate**** was dried and recrystallised from isopropanol to give 3-methyl-4(3-methylbutylamino)isoxazolo [5,4-d] pyrimidine (2.7 g, m.p. 133°), Compound no 29 of Table I.

Workup

  1. temperatureIt was then cooled
  2. customThe precipitate**** was dried
  3. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-c9790dcda15f4377813235a01094da63
Source dataset
uspto-grants-1980_02
Patent number
US04189483

Reaction notes

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