tert-Butyl carbamate → HCID 178517110, compound

HRID 2203268Notes

Reaction equation

HRID 2203268 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][CH2:9]2)=[CH:4][CH:3]=1.[C:20](=O)([O:22]C(C)(C)C)[NH2:21]>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][N:12]3[C:20](=[O:22])[NH:21][C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:11]3=[N:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 77922tert-Butyl carbamateHCID 86702438HCID 86702438, compound

Product 1

HCID 178517110HCID 178517110, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(4-chlorophenyl)-2-phenyl-1,4,5,6-tetrahydropyrimidine (12.9 mg, 0.048 mmol), tert-butyl carbamate (16.7 mg, 0.143 mmol) and copper(II) acetate (8.7 mg, 0.048 mmol) in 0.6 mL DMF was heated at 100° C. in a sealed reaction vessel under an oxygen gas atmosphere. After 1 hour the DMF solvent was evaporated and the residue chromatographed eluting with 5% MeOH/CHCl3 to give the title compound as a pale yellow solid (1.8 mg, 12%). 1H NMR (Acetone-d6) δ: 9.54 (br. s, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.36-7.49 (m, 5H), 7.05-7.13 (m, 2H), 4.32-4.41 (m, 1H), 3.79-3.89 (m, 1H), 3.54-3.71 (m, 2H), 3.05-3.20 (m, 1H).

Workup

  1. customAfter 1 hour the DMF solvent was evaporated
  2. customthe residue chromatographed
  3. washeluting with 5% MeOH/CHCl3

Sources & evidence

ORD record
ord-a3655fe32670447f9def697956bf1c4d
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

Loading…