Isopropanol → Methyl 2-[6-amino-3-chloro-5-nitropyrazin-2-yl]-3-(2,3-dihydroxypropyl)amino-2-butenoate

HRID 1903069Notes

Reaction equation

HRID 1903069 reaction equation
C(O)(C)C.[OH:5][CH:6]([CH2:16][OH:17])[CH2:7][NH:8][C:9]([CH3:15])=[CH:10][C:11]([O:13][CH3:14])=[O:12].[Cl:18][C:19]1[N:20]=[C:21]([N+:27]([O-:29])=[O:28])[C:22]([NH2:26])=[N:23][C:24]=1Cl>C(N(CC)CC)C>[NH2:26][C:22]1[N:23]=[C:24]([C:10](=[C:9]([NH:8][CH2:7][CH:6]([OH:5])[CH2:16][OH:17])[CH3:15])[C:11]([O:13][CH3:14])=[O:12])[C:19]([Cl:18])=[N:20][C:21]=1[N+:27]([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 130629765,6-Dichloro-3-nitropyrazin-2-amineHCID 71430100Methyl 3-[(2,3-dihydroxypropyl)amino]but-2-enoate

Product 1

HCID 86739300Methyl 2-[6-amino-3-chloro-5-nitropyrazin-2-yl]-3-(2,3-dihydroxypropyl)amino-2-butenoate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 75 ml of isopropanol is added 3.3 g (0.017 m) methyl 3-(2,3-dihydroxypropyl)amino-2-butenoate (3), 4.18 g (0.02 m) 5,6-dichloro-3-nitropyrazinamine (5), and 2.0 g (0.02 m) triethylamine. This solution is heated at 60°-65° for two days. The reaction mixture is then stripped on the rotary evaporator and the residue chromatographed on silica gel eluted with 12% methanol/chloroform. Material with Rf =0.5 is collected and after crystallization from acetonitrile the desired product is an orange solid, m.p. 184°-186° (dec).

Workup

  1. temperatureThis solution is heated at 60°-65° for two days
  2. customThe reaction mixture is then stripped on the rotary evaporator
  3. customthe residue chromatographed on silica gel
  4. washeluted with 12% methanol/chloroform
  5. customMaterial with Rf =0.5 is collected
  6. customafter crystallization from acetonitrile the desired product

Sources & evidence

ORD record
ord-8ead199c3d1740aeb87e29090686af52
Source dataset
uspto-grants-1984_03
Patent number
US04435400

Reaction notes

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