N,N-Dimethylethylenediamine → HCID 20183316, compound

HRID 255723Notes

Reaction equation

HRID 255723 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=2[S:23][CH3:24])[C:3]=1C(O)=O.C1(P([N:42]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:45][N:46]([CH3:50])[CH2:47][CH2:48][NH2:49].[C:51](=[O:54])([O-])O.[Na+]>C1C=CC=CC=1.C(OCC)C.C(N(CC)CC)C>[CH3:45][N:46]([CH3:50])[CH2:47][CH2:48][NH:49][C:51](=[O:54])[NH:42][C:3]1[C:4]([C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=2[S:23][CH3:24])=[N:5][C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:7][C:2]=1[CH3:1]

Participants

8

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 20183359HCID 20183359, compound

Product 1

HCID 20183316HCID 20183316, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 6-methyl-4-(2-methylthio-5-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylic acid (12.5 g), triethylamine (4.57 ml) and diphenylphosphorylazide (7.07 ml) in benzene (125 ml) was refluxed for 2 hours and to the reaction mixture was added 2-dimethylaminoethylamine (3.47 g). After the reflux was continued for 2 hours, the reaction mixture was poured into a mixture of a diethyl ether (100 ml) and saturated sodium hydrogen carbonate. The separated organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on alumina eluting with chloroform. The fractions containing the desired product were combined and concentrated in vacuo. The residue was recrystallized from diethyl ether to afford 5-[3-(2-dimethylaminoethyl)ureido]-6-methyl-4-(2-methylthio-5-nitrophenyl)-2-phenylpyrimidine.

Workup

  1. temperaturewas refluxed for 2 hours and to the reaction mixture
  2. dry with materialThe separated organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on alumina eluting with chloroform
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-6612c04dc44e4829a6b9386eab3abd65
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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