1-Isocyanato-3-phenoxybenzene → 1-(2-t-Butyl-4-phenylpyrimidin-5-yl)-3-(3-phenoxyphenyl)urea

HRID 1696577Notes

Reaction equation

HRID 1696577 reaction equation
Cl.[C:2]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([NH2:18])=[CH:8][N:7]=1)([CH3:5])([CH3:4])[CH3:3].[N:19]([C:22]1[CH:23]=[C:24]([CH:32]=[CH:33][CH:34]=1)[O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[C:20]=[O:21]>>[C:2]([C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9]([NH:18][C:20]([NH:19][C:22]2[CH:34]=[CH:33][CH:32]=[C:24]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=2)=[O:21])=[CH:8][N:7]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 34456731-Isocyanato-3-phenoxybenzeneHCID 672717522-t-Butyl-4-phenylpyrimidin-5-amine hydrochloride

Product 1

HCID 588516711-(2-t-Butyl-4-phenylpyrimidin-5-yl)-3-(3-phenoxyphenyl)ureaYield 25.3%

Procedure

Using general method A, 2-t-butyl-4-phenylpyrimidin-5-amine hydrochloride (100 mg, 0.379 mmol, available from Example 279) and 1-(3-isocyanatophenoxy)benzene (88 mg, 0.417 mmol) were combined to yield 1-(2-t-butyl-4-phenylpyrimidin-5-yl)-3-(3-phenoxyphenyl)urea (42 mg, 25% yield). 1H NMR (DMSO-d6): δ 1.38 (s, 9H), 6.61-6.63 (m, 1H), 7.01-7.56 (m, 1H), 7.73-7.75 (m, 2H), 8.10 (s, 1H), 9.02 (s, 1H), 9.19 (s, 1H). LC-MS (EI) m/z: 439.3 (M+H+).

Sources & evidence

ORD record
ord-c841411cc5f540419e954abd385fece9
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

Loading…