Dimethylformamide → HCID 70454158, compound

HRID 365194Notes

Reaction equation

HRID 365194 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]1O[CH2:3]1.[NH2:12][CH2:13][CH2:14][NH:15][C:16]1[N:17]([CH2:27][CH3:28])[C:18](=[O:26])[N:19]([CH2:24][CH3:25])[C:20](=[O:23])[C:21]=1[CH3:22].CN(C)C=O.[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>C(OCC)(=O)C.O>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([O:39][CH:2]([CH2:3][NH:12][CH2:13][CH2:14][NH:15][C:16]1[N:17]([CH2:27][CH3:28])[C:18](=[O:26])[N:19]([CH2:24][CH3:25])[C:20](=[O:23])[C:21]=1[CH3:22])[CH2:1][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:38]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 31217Phenyl glycidyl etherHCID 444972Fumaric AcidHCID 20237811HCID 20237811, compound

Product 1

HCID 70454158HCID 70454158, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3.8 g. Phenyl glycidyl ether and 9.8 g. 4-(2-aminoethylamino)-5-methyl-1,3-diethylpyrimidine-2,6(1H,3H)-dione are dissolved in 10 ml. dimethylformamide and left to stand for 24 hours at ambient temperature. The reaction mixture is then poured into water, extracted with methylene chloride, dried and chromatographed on silica gel using, as elution agent, methylene chloridemethanol (9:1 v/v). The yellowish oil (6.8 g.) obtained by evaporation of the pure fractions is dissolved in ethyl acetate, whereafter a solution of 2.1 g. fumaric acid in ethyl acetate is added thereto. The crystalline precipitate obtained is filtered off with suction and washed with ethyl acetate. There are obtained 5.4 g. (42% of theory) of the desired product in the form of colorless crystals which melt at 141°-142° C., with bubble formation.

Workup

  1. extractionextracted with methylene chloride
  2. customdried
  3. customchromatographed on silica gel using, as elution agent, methylene chloridemethanol (9:1 v/v)
  4. customThe yellowish oil (6.8 g.) obtained by evaporation of the pure fractions
  5. customThe crystalline precipitate obtained
  6. filtrationis filtered off with suction
  7. washwashed with ethyl acetate
  8. customThere are obtained 5.4 g

Sources & evidence

ORD record
ord-1d43057c909b4b24a9d03ada1da907b7
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

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