Ethanol → 3-Methyl-4-(2-indanylamino)isoxazolo[5,4-d]pyrimidine

HRID 1581972Notes

Reaction equation

HRID 1581972 reaction equation
[C:1]([C:3]1[C:4](N)=[N:5][O:6][C:7]=1[N:8]=[CH:9]OCC)#[N:2].[NH2:14][CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1.[CH2:24](O)C>>[CH3:24][C:4]1[C:3]2[C:7](=[N:8][CH:9]=[N:2][C:1]=2[NH:14][CH:15]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16]2)[O:6][N:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 763102-AminoindaneHCID 540873914-Cyano-5-ethoxymethyleneamino-3-aminoisoxazole

Product 1

HCID 227195823-Methyl-4-(2-indanylamino)isoxazolo[5,4-d]pyrimidine

Procedure

4-cyano-5-ethoxymethyleneamino-3-aminoisoxazole (320 mg, 1.8 mmol) (see J. Org. Chem., 29, 2116 (1964)) and 2-aminoindan (710 mg, 5.3 mmol) in dry ethanol (3 ml) were heated to reflux for 1.5 hours. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=2:1). The product obtained was crystallized from ethanol to obtain the title compound (270 mg, 0.38 mmol) having the following physical properties:

Workup

  1. temperatureto reflux for 1.5 hours
  2. customThe residue obtained
  3. distillationby distilling off the solvent under reduced pressure
  4. customwas purified by silica gel chromatography (hexane:ethyl acetate=2:1)
  5. customThe product obtained
  6. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-fc84f73a7e0e4e1882b9982d85240895
Source dataset
uspto-grants-2004_05
Patent number
US06734180B1

Reaction notes

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