Acetic Acid → 4-(2-Indanylamino)furo[2,3-d]pyrimidine

HRID 1581969Notes

Reaction equation

HRID 1581969 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8].[CH:9](OCC)(OCC)OCC.[NH2:19][CH:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1.C([O-])(=O)C.[Na+].C(O)(=O)C>C(OC(=O)C)(=O)C>[CH2:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:28][CH:20]1[NH:19][C:7]1[C:6]2[CH:5]=[CH:4][O:3][C:2]=2[N:1]=[CH:9][N:8]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 763102-AminoindaneHCID 517045Sodium AcetateHCID 227196132-Amino-3-cyanofuran

Product 1

HCID 227195994-(2-Indanylamino)furo[2,3-d]pyrimidineYield 7.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideCatalyst

Conditions

Temperature
130 °C

Procedure

A mixture of 2-amino-3-cyanofuran (270 mg, 2.5 mmol), triethyl orthoformate (1.5 ml, 9.0 mmol), and acetic anhydride (0.18 ml, 1.9 μmol) was heated to reflux at 130° C. for 2 hours. The reaction mixture was cooled, and 2-aminoindan (670 mg, 5.0 mmol), sodium acetate (640 mg, 7.8 mmol), and acetic acid (1.1 ml, 19 mmol) were added, which was further heated to reflux at 130° C. for 2 hours. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to obtain the title compound (44 mg, 0.18 mmol) having the following physical properties:

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. temperaturewhich was further heated
  4. temperatureto reflux at 130° C. for 2 hours
  5. customThe residue obtained
  6. distillationby distilling off the solvent under reduced pressure
  7. customwas purified by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-288706d30cd34083ad410c026f551546
Source dataset
uspto-grants-2004_05
Patent number
US06734180B1

Reaction notes

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