N,N,N',N'-Tetramethylmethanediamine → HCID 13137363, compound

HRID 2166707Notes

Reaction equation

HRID 2166707 reaction equation
CN([CH2:4][N:5]([CH3:7])[CH3:6])C.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][S:14][CH2:15][CH2:16][NH:17][C:18]1[NH:23][C:22](=[O:24])[C:21]([CH2:25][C:26]2[O:27][CH:28]=[CH:29][CH:30]=2)=[CH:20][N:19]=1>C(O)(=O)C>[CH3:4][N:5]([CH2:7][C:12]1[O:8][C:9]([CH2:13][S:14][CH2:15][CH2:16][NH:17][C:18]2[NH:23][C:22](=[O:24])[C:21]([CH2:25][C:26]3[O:27][C:28]([CH2:7][N:5]([CH3:4])[CH3:6])=[CH:29][CH:30]=3)=[CH:20][N:19]=2)=[CH:10][CH:11]=1)[CH3:6]

Participants

4

Reactant 2

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 20498751HCID 20498751, compound

Product 1

HCID 13137363HCID 13137363, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bis-dimethylaminomethane (1.23 g,) was added whilst stirring 2-[2-(2-furanylmethylthio)ethylamino]-5-(2-furanylmethyl)-4-pyrimidone (0.8 g) was suspended in glacial acetic acid (8 ml). The mixture was then stirred at room temperature for 3 hr and allowed to stand for ca 16 hr. The acid was evaporated at reduced pressure azeotropically with water. The residual oil was dissolved in water, filtered and the filtrate taken to pH 9 using aqueous sodium carbonate solution. The basic solution was extracted using ethyl acetate, the extracts dried (MgSO4) and evaporated to give 2-[2-(5-dimethylaminomethyl-2-furanylmethylthio)ethylamino]-5-(5-dimethylaminomethyl-2-furanylmethyl)-4-pyrimidone as an oily residue (1.01 g). The oily residue was dissolved in a minimum volume of ethanol and then acidified with ethanolic hydrochloric acid. The acidic solution was then evaporated to dryness and the residual oil was crystallised from isopropanol/ethanol to give the white solid trihydrochloride salt (1.33 g) m.p. 177°-9° C.

Workup

  1. waitto stand for ca 16 hr
  2. customThe acid was evaporated at reduced pressure azeotropically with water
  3. dissolutionThe residual oil was dissolved in water
  4. filtrationfiltered
  5. extractionThe basic solution was extracted
  6. dry with materialthe extracts dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-02a3532349be433f8e8e46366bd96067
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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