Allylamine → HCID 89996015, compound

HRID 1480862Notes

Reaction equation

HRID 1480862 reaction equation
[Br:1][C:2]1[C:3]([C:10]([O:12]C)=O)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[CH2:14]([NH2:17])[CH:15]=[CH2:16]>CO>[CH2:14]([NH:17][C:10]([C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([S:8][CH3:9])[N:4]=1)=[O:12])[CH:15]=[CH2:16]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 2794729Methyl 5-bromo-2-(methylsulfanyl)pyrimidine-4-carboxylate

Product 1

HCID 89996015HCID 89996015, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate (Preparation 30, 1.00 g, 3.80 mmol) was dissolved in methanol (16 mL), treated with allylamine (3.00 mL, 40.0 mmol) and heated to 90° C. for 18 hours. The mixture was concentrated in vacuo and the residue purified by silica gel column chromatography eluting with 0 to 5% EtOAc in cyclohexanes to give the title compound (981 mg, 90%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by silica gel column chromatography
  3. washeluting with 0 to 5% EtOAc in cyclohexanes

Sources & evidence

ORD record
ord-a04ffff0649b427abeb922ce69b8175e
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

Loading…