2-Aminoindane → 7-(2-Indanylamino)oxazolo[5,4-d]pyrimidine

HRID 1581971Notes

Reaction equation

HRID 1581971 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][O:6][C:7]=1[N:8]=[CH:9]OCC)#[N:2].[NH2:13][CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1>C(O)C>[CH2:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH:14]1[NH:13][C:1]1[C:3]2[N:4]=[CH:5][O:6][C:7]=2[N:8]=[CH:9][N:2]=1

Participants

4

Reactant 2

HCID 763102-AminoindaneHCID 54245542HCID 54245542, compound

Product 1

HCID 227196087-(2-Indanylamino)oxazolo[5,4-d]pyrimidineYield 14.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-cyano-5-ethoxymethyleneaminooxazole (240 mg, 1.5 mmol) (see J. Am. Chem. Soc., 88, 3829 (1966), Bull. Chem. Soc. JAPAN, 43, 187 (1970), Bull. Chem. Soc. JAPAN, 43, 3909 (1970)) and 2-aminoindan (580 mg, 4.4 mmol) in dry ethanol (2 ml) were heated to reflux for 6.5 hours. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (methylene chloride:ethyl acetate=1:4) to obtain the title compound (56 mg, 0.22 mmol) having the following physical properties:

Workup

  1. temperatureto reflux for 6.5 hours
  2. customThe residue obtained
  3. distillationby distilling off the solvent under reduced pressure
  4. customwas purified by silica gel chromatography (methylene chloride:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-d6166fb11d0e4d8c998ccc45e64de9a5
Source dataset
uspto-grants-2004_05
Patent number
US06734180B1

Reaction notes

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