Sodium Methoxide → HCID 18507453, compound

HRID 1356133Notes

Reaction equation

HRID 1356133 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10](Br)=[CH:11][CH:12]=2)[C:5]([C:14]#[N:15])=[C:4]([S:16][CH3:17])[N:3]=1.[CH3:18][O-:19].[Na+]>COCCOC>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10]([O:19][CH3:18])=[CH:11][CH:12]=2)[C:5]([C:14]#[N:15])=[C:4]([S:16][CH3:17])[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18507285HCID 18507285, compound

Product 1

HCID 18507453HCID 18507453, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 493 mg (1.58 mmol) 2-amino-4-(5-bromo-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile in 10 ml DME was added 2.1 ml (11,3 mmol) sodium methylate solution (5.4M in methanol) and the mixture heated at 50° C. for 1 h. The reaction mixture was then poured into 100 ml ice-water and the resulting precipitate collected by filtration and washed with water. Chromatography (ethyl acetate/hexane 1/1) afforded 363 mg (87%) 2-amino-4-(5-methoxy-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 262 (M+, 100).

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-715e1473314b4512b7ce9584784ea5b8
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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