O-Methyltyramine → Furo[2,3-d]pyrimidin-4-amine, N-[2-(4-methoxyphenyl)ethyl]-5-methyl-

HRID 375517Notes

Reaction equation

HRID 375517 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[CH2:10](OC(OCC)OCC)C.C(OC(=O)C)(=O)C.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][NH2:37])=[CH:31][CH:30]=1.C([O-])(=O)C.[Na+]>CCOCC.O>[CH3:9][C:5]1[C:6]2[C:7]([NH:37][CH2:36][CH2:35][C:32]3[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=3)=[N:8][CH:10]=[N:1][C:2]=2[O:3][CH:4]=1

Participants

8

Reactant 5

HCID 4657O-MethyltyramineHCID 7918Acetic Anhydride2×HCID 31214Ethyl orthoformateHCID 517045Sodium AcetateHCID 110188532-AMINO-4-METHYL-3-FURONITRILE

Product 1

HCID 164420Furo[2,3-d]pyrimidin-4-amine, N-[2-(4-methoxyphenyl)ethyl]-5-methyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4 g of 2-amino-3-cyano-4-methylfuran, 3 mL of triethylorthoformate and 0.5 mL of acetic anhydride was heated at 135° C. for three hours. To the hot solution was added 4.5 g of 2-(4-methoxyphenyl)ethylamine, 5 mL of acetic anhydride, and 3.1 g of sodium acetate. The temperature of the mixture was kept at 135° C. for three additional hours, then the mixture was cooled and combined with a mixture of water and ether. The ether layer was separated, and product was extracted from the remaining aqueous layer with large volumes of ether. The ether extracts were combined, dried over magnesium sulfate, filtered, and concentrated. The residue was recrystallized from acetone/ether. Yield 2.6 g. M.P. 184° C.

Workup

  1. customwas kept at 135° C. for three additional hours
  2. temperaturethe mixture was cooled
  3. customThe ether layer was separated
  4. extractionproduct was extracted from the remaining aqueous layer with large volumes of ether
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized from acetone/ether

Sources & evidence

ORD record
ord-2e882549bc91403ba9e102711a1cfee6
Source dataset
uspto-grants-1996_01
Patent number
US05486516

Reaction notes

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