Triethylamine → HCID 68732381, compound

HRID 1523236Notes

Reaction equation

HRID 1523236 reaction equation
[C:1]1([C@@:7]([NH2:19])([CH3:18])[CH2:8][CH2:9][NH:10][C:11]2[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH3:18][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][N:10]([C:11]2[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=2)[C:28](=[O:30])[NH:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 59627237HCID 59627237, compound

Product 1

HCID 68732381HCID 68732381, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-3-phenyl-N1-m-tolylbutane-1,3-diamine (50 mg, 0.2 mol) and Et3N (60 mg, 0.6 mmol) in CH2Cl2 (3 mL) was added triphosgene (24 mg, 0.08 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 2 h and concentrated. The residue was purified by preparative HPLC to give 4-methyl-4-phenyl-1-m-tolyl-tetrahydro-pyrimidin-2-one (8 mg, 14%). LC-MS Method 1 tR=1.13 min, m/z=281; 1H NMR (CDCl3): 1.65 (s, 3H), 2.15-2.23 (m, 1H), 2.25 (s, 3H), 2.27-2.47 (m, 1H), 3.20-3.22 (t, 1H), 3.37-3.40 (d, 1H), 6.89-6.92 (m, 2H), 6.99-7.01 (m, 1H), 7.15-7.17 (m, 1H), 7.25-7.27 (m, 1H), 7.7.31-7.38 (m, 4H), 7.83 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-be31c8cd5bf34311bd6736c9b7eb9899
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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