Triethylamine → HCID 59627202, compound

HRID 1523259Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][CH2:11][CH2:12][C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([NH2:18])[CH2:14][C:15]([CH3:17])=[CH2:16])[CH3:9])=[CH:4][CH:3]=1.CCN(CC)CC.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:11][CH2:12][C@:13]([CH2:14][C:15]([CH3:17])=[CH2:16])([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:18][C:33]2=[O:35])[CH3:9])=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 94429Triphosgene

HCID 72343000HCID 72343000, compound

Product 1

HCID 59627202HCID 59627202, compoundYield 133.1%

Procedure

To a solution of N1-[1-(4-Bromo-phenyl)-ethyl]-5-methyl-3-phenyl-hex-5-ene-1,3-diamine (2.97 g, 0.007 mol) and Et3N (3.53 g, 0.035 mol) was added triphosgene (0.58 g, 0.002 mol) at 0° C. The resulting mixture was stirred for 3 h. The mixture was washed with water, the organic layer was separated, and concentrated to give the crude (R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-methylallyl)-4-phenyltetrahydropyrimidin-2(1H)-one (1.1 g, 40%). which was purified by column chromatography. 1H NMR (CDCl3): δ=1.24 (s, 3H), 1.38 (m, 1H), 1.43 (d, 3H), 1.56 (m, 1H), 1.88 (m, 1H), 2.09 (m, 1H), 2.12 (m, 1H), 2.44 (m, 1H), 2.64 (m, 2H) 4.72 (s, 1H), 4.83 (s, 1H), 5.21 (s, 1H), 5.74 (m, 1H), 6.90 (m, 2H), 6.92-7.14 (m, 2H), 7.18-7.38 (m, 5H).

Workup

washThe mixture was washed with water
customthe organic layer was separated
concentrationconcentrated

Sources & evidence

ORD record: ord-22f753d982634ecdb3b3490dcbc08c4f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079861B2

Reaction notes

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