Triethylamine → 2-(2,3-Dihydroxypropyl)amino-5-nitropyrazine

HRID 247573

Reaction equation

HRID 247573 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:18][CH2:19][CH:20]([OH:23])[CH2:21][OH:22]>C(#N)C.C(O)(C)C>[OH:23][CH:20]([CH2:21][OH:22])[CH2:19][NH:18][C:2]1[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 735613-Amino-1,2-propanediolHCID 15020582-Chloro-5-nitropyrazine

Product 1

HCID 159142402-(2,3-Dihydroxypropyl)amino-5-nitropyrazine

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.5 g (0.003 mol) 6 and 0.3 g (0.003 mol) triethylamine in 10 ml acetonitrile is added 0.32 g (0.0035 mol) 3-amino-1,2-propanediol (10) in 10 ml iso-propanol. After stirring for 18 hours at room temperature the solvent is removed on the rotary evaporator and the residue is purified by flash chromatography on silica gel eluting with 10% methanol/chloroform. Pure 12 has Rf 0.4 and is a pale yellow solid, m.p. 185°-7°.

Workup

  1. customis removed on the rotary evaporator
  2. customthe residue is purified by flash chromatography on silica gel eluting with 10% methanol/chloroform

Sources & evidence

ORD record
ord-07d5245d240a4541a92dcefed48e24e7
Source dataset
uspto-grants-1987_11
Patent number
US04709035

Linked notes

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