Benzene → Methyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrimidine-5-carboxylate

HRID 42182Notes

Reaction equation

HRID 42182 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[CH:25]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>C(O)(=O)C>[CH3:25][O:21][C:20]([C:17]1[CH:16]=[N:15][C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]2)=[N:19][CH:18]=1)=[O:22]

Participants

6

Reactant 4

HCID 241BenzeneHCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 541814542-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrimidine-5-carboxylic acid

Product 1

HCID 59240679Methyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrimidine-5-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 2-(4-tert-Butoxycarbonyl-piperazin-1-yl)-pyrimidine-5-carboxylic acid (150 mg, 0.486 mmol) in an oven dried round-bottom flask is added methanol (1.0 mL) and benzene (3.7 mL) under nitrogen, and the reaction stirred for 10 min. Trimethylsilyldiazomethane (0.34 ml, 0.678 mmol) is added and the reaction stirred for 1 h. Glacial acetic acid (0.05 ml) is then added until the yellow color has disappeared. The reaction mixture is concentrated under reduced pressure and co-evaporated with benzene. It is dried under high vacuum to yield the title compound as a white solid (155 mg, 99% yield).

Workup

  1. stirringthe reaction stirred for 1 h
  2. concentrationThe reaction mixture is concentrated under reduced pressure and co-evaporated with benzene
  3. customIt is dried under high vacuum

Sources & evidence

ORD record
ord-c59dfa5d97884f95804e44b6da109058
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

Loading…