4-Fluorobenzylamine → HCID 178453347, compound

HRID 1013009Notes

Reaction equation

HRID 1013009 reaction equation
[CH2:1]([N:8]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:9][CH2:10][C:11]1[N:16]=[C:15]([C:17]([O:19]C)=O)[C:14]([OH:21])=[C:13]([OH:22])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>CO>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]1[N:16]=[C:15]([C:17]([NH:36][CH2:35][C:34]2[CH:37]=[CH:38][C:31]([F:30])=[CH:32][CH:33]=2)=[O:19])[C:14]([OH:21])=[C:13]([OH:22])[N:12]=1)[C:23](=[O:24])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 178499091HCID 178499091, compound

Product 1

HCID 178453347HCID 178453347, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude methyl 2-{2-[benzyl(tert-butoxycarbonyl)amino]ethyl}-5,6-dihydroxypyrimidine-4-carboxylate (prepared as described in Step 2) was dissolved in methanol and treated with p-fluorobenzylamine (2.5 equivalents) at 80° C. for 12 hours. The mixture was then cooled to room temperature, volatiles were evaporated and the residue was poured in EtOAc and washed 0.5 N HCl and brine. The organic phase was dried (Na2SO4), filtered and concentrated to a brown solid residue. MS (ES) C26H29FN4O5 requires 496. Found: 497 (M+H+).

Workup

  1. customvolatiles were evaporated
  2. additionthe residue was poured in EtOAc
  3. washwashed 0.5 N HCl and brine
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a brown solid residue

Sources & evidence

ORD record
ord-5e40d035c3a14aaf869657474304355c
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

Loading…