Pyridine → HCID 86739325, compound

HRID 365195Notes

Reaction equation

HRID 365195 reaction equation
Cl[C:2]1[N:3]([CH3:12])[C:4](=[O:11])[N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].[O:13]([CH2:20][CH:21]([OH:29])[CH2:22][N:23]([CH2:25][CH2:26][NH:27][CH3:28])[CH3:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>C(Cl)Cl>[O:13]([CH2:20][CH:21]([OH:29])[CH2:22][N:23]([CH2:25][CH2:26][N:27]([C:2]1[N:3]([CH3:12])[C:4](=[O:11])[N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8])[CH3:28])[CH3:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 132969876-Chloro-1,3,5-trimethyl-2,4(1H,3H)-pyrimidinedioneHCID 20237846HCID 20237846, compound

Product 1

HCID 86739325HCID 86739325, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.7 g. 4-Chloro-1,3,5-trimethylpyrimidine-2,6(1H,3H)-dione and 6.0 g. 1-phenoxy-3-(2-methylaminoethyl-N-methylamino)-propan-2-ol (b.p. 138°-142° C./0.01 mm.Hg; obtained from phenyl glycidyl ether and N,N'-dimethylethylenediamine) are stirred for 72 hours at 80° C. in 10 ml. pyridine. The reaction mixture is then dissolved in methylene chloride, washed with water, dried and chromatographed on silica gel using, as elution agent, methylene chloride-methanol (20:1 v/v). By evaporation of the pure fractions, there are obtained 3.0 g. (31% of theory) of the desired product in the form of an almost colorless oil.

Workup

  1. washwashed with water
  2. customdried
  3. customchromatographed on silica gel using, as elution agent, methylene chloride-methanol (20:1 v/v)
  4. customBy evaporation of the pure fractions, there
  5. customare obtained 3.0 g

Sources & evidence

ORD record
ord-2f00dfb6d7e240338c492e1396988c60
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

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