4,6-Dimethyl-2-(4-nitrobenzyloxycarbonylthio)pyrimidine → 3-(p-Nitrobenzyloxycarbonyl)aminomethylbenzyl alcohol

HRID 1252223Notes

Reaction equation

HRID 1252223 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].[N+:11]([C:14]1[CH:32]=[CH:31][C:17]([CH2:18][O:19][C:20](SC2N=C(C)C=C(C)N=2)=[O:21])=[CH:16][CH:15]=1)([O-:13])=[O:12]>O1CCCC1>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][O:19][C:20]([NH:7][CH2:6][C:5]2[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=2)[CH2:2][OH:1])=[O:21])=[CH:31][CH:32]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 135043164,6-Dimethyl-2-(4-nitrobenzyloxycarbonylthio)pyrimidineHCID 21880609[3-(Aminomethyl)phenyl]methanol

Product 1

HCID 540539623-(p-Nitrobenzyloxycarbonyl)aminomethylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 3-hydroxymethylbenzylamine (1.37 g) in tetrahydrofuran (30 ml), a solution of S-p-nitrobenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (6.2 g) in tetrahydrofuran (20 ml) was added at room temperature, followed by stirring for 1 hours. The resulting precipitates were removed by filtration and the filtrate was diluted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and evaporated in vacuo to give an oily residue which was then crystallized from diethyl etherdichloromethane to give 3-(p-nitrobenzyloxycarbonyl)aminomethylbenzyl alcohol.

Workup

  1. customThe resulting precipitates
  2. customwere removed by filtration
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customto give an oily residue which
  8. customwas then crystallized from diethyl etherdichloromethane

Sources & evidence

ORD record
ord-7822ed32ed3a4e20ab8061e3bff0feaf
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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