2-Amino-2-methyl-1,3-propanediol → HCID 22457909, compound

HRID 2184775Notes

Reaction equation

HRID 2184775 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][C:8]([C:11]([O:13]C)=O)=[CH:7][N:6]=1)=[O:4].[NH2:15][C:16]([CH3:21])([CH2:19][OH:20])[CH2:17][OH:18]>C(O)C>[OH:18][CH2:17][C:16]([NH:15][C:11]([C:8]1[CH:7]=[N:6][C:5]([C:3]([NH:15][C:16]([CH3:21])([CH2:19][OH:20])[CH2:17][OH:18])=[O:4])=[CH:10][N:9]=1)=[O:13])([CH3:21])[CH2:19][OH:20]

Participants

4

Reactant 2

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 518685Dimethyl pyrazine-2,5-dicarboxylate

Product 1

HCID 22457909HCID 22457909, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 500 mg of 2,5-dimethoxycarbonylpyrazine and 525 mg of 2-amino-2-methyl-1,3-propanediol in 3 cm3 of ethanol is heated at a temperature in the region of the reflux temperature for 90 minutes. The reaction mixture is filtered while hot. The white solid is washed with 5 cm3 of boiling ethanol. 200 mg of N,N′-bis(1,3-dihydroxy-2-methyl-2-propyl)pyrazine-2,5-dicarboxamide are thus obtained in the form of a white solid melting at 208° C. [1H NMR spectrum (400 MHz, CDCl3, δ at ppm): 1.34 (s, 6H: 2×CH3); 3.55 and 3.66 (2 dd, J=11 and 5.5 Hz, 8H: 4×OCH2); 5.01 (t, J=5.5 Hz, 4H: 4×OH); 8.22 (s, 2H: ═CH at 3 and ═CH at 6); 9.20 (s, 2H: 2×CONH)].

Workup

  1. filtrationThe reaction mixture is filtered while hot
  2. washThe white solid is washed with 5 cm3 of boiling ethanol

Sources & evidence

ORD record
ord-131b8357ff934c6b85f72c68970be822
Source dataset
uspto-grants-2002_06
Patent number
US06399613B1

Reaction notes

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