Water → (3,5-Diamino-6-(2,3,5-trichlorophenyl)pyrazin-2-yl)methanol

HRID 1383326Notes

Reaction equation

HRID 1383326 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:12]=2[Cl:19])[C:6]([NH2:10])=[N:7][C:8]=1[NH2:9])=[O:2].[BH4-].[Na+].O>C(O)C>[OH:2][CH2:1][C:3]1[N:4]=[C:5]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:12]=2[Cl:19])[C:6]([NH2:10])=[N:7][C:8]=1[NH2:9]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 181802065-Formyl-2,6-Diamino-3-(2,3,5-trichlorophenyl)pyrazine

Product 1

HCID 18180197(3,5-Diamino-6-(2,3,5-trichlorophenyl)pyrazin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 5-Formyl-2,6-Diamino-3-(2,3,5-trichlorophenyl)pyrazine (0.198 g, 6.24×10−4 mole) in ethanol (100 ml) was added sodium borohydride (0.0359, 9.35×10−4 mole) at room temperature. The reaction was stirred at room temperature under nitrogen for 1 hr, water (1 ml) was added and the solution evaporated in vacuo. The residue was dissolved in ethyl acetate (200 ml), washed with brine, dried over magnesium sulphate, filtered and evaporated in vacuo. The product was purified by ‘flash chromatography’ using 11-40% ethyl acetate in cyclohexane as the eluent. Yield 0.104 g (52%), M.p. 185-186° C. N.m.r. (D6DMSO) δ: 4.32 (2H, d), 4.98 (1H, t), 5.56 (2H, s), 5.85 (2H, s), 7.30 (1H, d), 7.76 (1H, d).

Workup

  1. customthe solution evaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (200 ml)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe product was purified by ‘flash chromatography’

Sources & evidence

ORD record
ord-d058e24159894ac39ec2173b91d6daad
Source dataset
uspto-grants-2001_07
Patent number
US06255307B1

Reaction notes

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