Methanol → 5,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

HRID 1099103Notes

Reaction equation

HRID 1099103 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[C:5]([O:12][CH3:13])=[CH:4][N:3]=1.[CH3:14][O-:15].[Na+].CO>C(#N)C>[CH3:14][O:15][C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[C:5]([O:12][CH3:13])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 56949576HCID 56949576, compound

Product 1

HCID 114468885,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amineYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Chloro-8-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine (4; 100 mg, 0.50 mmol) was suspended in acetonitrile (5 mL) at room temperature and treated with 25% sodium methoxide in methanol (200 mg, 2 eq). The resulting slurry was stirred at room temperature for 1.5 hours and then filtered. The solids were washed with water and dried to afford the title compound as a chalk-colored solid (87 mg, 88%) that was identical in HPLC retention to authentic 5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine (5): mp 185-186° C.; 1H NMR (DMSO-d6) δ 7.48 (s, 1H), 6.38 (br s, 2H), 4.04 (s, 3H), 3.88 (s, 3H); EIMS m/z 195.

Workup

  1. filtrationfiltered
  2. washThe solids were washed with water
  3. customdried

Sources & evidence

ORD record
ord-c3329b98ef704a1d8fb9eeb6e686e277
Source dataset
uspto-grants-2012_03
Patent number
US08143395B2

Reaction notes

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