trans-2-Phenylcyclopropyl isocyanate → (+/-)-trans-N-(4-(4-Ethylaminopyrimidin-6-yl-oxy)-phenyl)-N'-(2-phenyl-cyclopropyl)-urea

HRID 1993523Notes

Reaction equation

HRID 1993523 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)[N:7]=[CH:6][N:5]=1)[CH3:2].[C:18]1([C@@H:24]2[CH2:26][C@H:25]2[N:27]=[C:28]=[O:29])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:17]=[CH:16][C:14]([NH:15][C:28]([NH:27][C@@H:25]3[CH2:26][C@H:24]3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:29])=[CH:13][CH:12]=2)[N:7]=[CH:6][N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 255285trans-2-Phenylcyclopropyl isocyanateHCID 586593854-(4-Ethylaminopyrimidin-6-yloxy)aniline

Product 1

HCID 68535936(+/-)-trans-N-(4-(4-Ethylaminopyrimidin-6-yl-oxy)-phenyl)-N'-(2-phenyl-cyclopropyl)-urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-ethylaminopyrimidin-6-yl-oxy)-aniline (Stage 89.1; 271 mg, 1.177 mmol) In THF (5 ml) under N2-atmosphere, trans-2-phenyl-cyclopropyl-isocyanate (188 mg, 1.18 mmol; Aldrich) Is added. Then the solution is stirred for 8 h, whereas a precipitate is formed. Filtration and washing with THF and ether yields the title compound: m.p.: 205-206° C.; 1H-NMR (DMSO-d6): 8.50 (s, HN), 8.11 (s, 1H), 7.42 (d, 2H), 7.27 (m, 3H), 7.15 (m, 3H), 7.01 (d, 2H), 6.67 (s, HN), 5.67 (s, 1H), 3.25 (m, 2H), 2.74 (m, 1H), 1.98 (m, 1H), 1.17 (m, 2H), 1.09 (t, 3H); Anal.: CHN.

Workup

  1. customis formed
  2. filtrationFiltration
  3. washwashing with THF and ether

Sources & evidence

ORD record
ord-05d935c7ef5f4efd863c57dd4a730c3b
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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