Triethylamine → Methyl 6-[(2,3-dihydroxypropyl)amino]-3-nitropyrazine-2-carboxylate

HRID 64612

Reaction equation

HRID 64612 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([N+:12]([O-:14])=[O:13])=[N:4][CH:3]=1.[NH2:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19].C(N(CC)CC)C>C(O)(C)C>[OH:20][CH:17]([CH2:18][OH:19])[CH2:16][NH:15][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([N+:12]([O-:14])=[O:13])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 735613-Amino-1,2-propanediolHCID 15914238Methyl 6-chloro-3-nitropyrazine-2-carboxylate

Product 1

HCID 15914243Methyl 6-[(2,3-dihydroxypropyl)amino]-3-nitropyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 1.0 g (0.004 mol) 9 in 15 ml isopropanol is added 0.36 g (0.004 mol) 10 and 0.4 g (0.004 mol) triethylamine at room temperature. The reaction mixture becomes reddish in color and is stirred at room temperature for 16 hours. The solvent is removed on the rotary evaporator and the residue is purified by flash chromatography on silica gel followed by elution with 10% methanol/chloroform. Pure 15 has Rf 0.4 and is obtained as a yellow solid, m.p. 107°-9°.

Workup

  1. customThe solvent is removed on the rotary evaporator
  2. customthe residue is purified by flash chromatography on silica gel
  3. washfollowed by elution with 10% methanol/chloroform
  4. customis obtained as a yellow solid, m.p. 107°-9°

Sources & evidence

ORD record
ord-454a61fe3d5d40748003eece1dae88cf
Source dataset
uspto-grants-1986_09
Patent number
US04609659

Linked notes

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