Methyl chloroacetate → HCID 20061209, compound

HRID 1085285Notes

Reaction equation

HRID 1085285 reaction equation
[CH3:1][N:2]1[C:7]([NH:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[CH:6][C:5](=[O:25])[N:4]([CH3:26])[C:3]1=[O:27].Cl[CH2:29][C:30]([O:32][CH3:33])=[O:31].C(N(CC)CC)C>CS(C)=O.C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:7]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:6][C:5](=[O:25])[N:4]([CH3:26])[C:3]1=[O:27]

Participants

6

Reactant 3

HCID 7295Methyl chloroacetateHCID 8471TriethylamineHCID 20061439HCID 20061439, compound2×

Product 1

HCID 20061209HCID 20061209, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Procedure

1.5 g of 1,3-dimethyl-6-{2-[3-(4-nitroanilino)propylamino]ethylamino}-2,4(1H,3H)-pyrimidinedione (Compound b) obtained in the above procedure (3) were dissolved in 12 ml of DMSO, followed by the addition of 1.2 g of methyl chloroacetate and 1.5 ml of triethylamine. The resultant mixture was stirred at 50° C. for 2 hours, dissolved in chloroform, washed with water and then dried over anhydrous sodium sulfate. The solvent was thereafter distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (eluent: chloroform/methanol=30/1, by volume), thereby obtaining 1.8 g of 1,3-dimethyl-6-{2-[N-methoxycarbonylmethyl-3-(4-nitroanilino)propylamino]ethylamino}-2,4(1H,3H)-pyrimidinedione.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was thereafter distilled off under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (eluent: chloroform/methanol=30/1, by volume)

Sources & evidence

ORD record
ord-7507ccaf09df4f92a8df8c03165b65c4
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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