Sodium Hydroxide → 4-methyl-N1-(5-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)benzene-1,3-diamine

HRID 2067881Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)=[CH:11][N:10]=2)=[CH:4][C:3]=1[N+:26]([O-])=O.O.O.Cl[Sn]Cl.[OH-].[Na+]>Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]([F:24])([F:25])[F:23])=[CH:19][CH:20]=3)=[CH:11][N:10]=2)=[CH:4][C:3]=1[NH2:26]

Participants

Conditions

Temperature: 100 °C

Procedure

N-(4-methyl-3-nitrophenyl)-5-(4-(trifluoromethoxy)phenyl)pyrimidin-2-amine 28b (7.53 mmol) and SnCl2.2H2O (33.2 mmol) are suspended in 6N HCl (40 mL). The mixture is heated at 100° C. for 3 h. The reaction vessel is chilled in an ice-water bath and 5% NaOH is added. The organic layer is extracted with EtOAc (3×50 mL), washed with brine (1×50 mL), dried over Na2SO4 and concentrated to afford 4-methyl-N1-(5-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)benzene-1,3-diamine 29b which is used without further purification. 1H NMR (400 MHz, d6-DMSO) δ 9.54 (s, 1H), 8.84 (s, 2H), 7.88 (d, J=8.8 Hz, 2H), 7.51 (d, J=8.0 Hz, 2H), 7.12 (d, J=2.4 Hz, 1H), 6.94 (dd, J=2.0 and 8.0 Hz, 1H), 6.88 (d, J=8.4 Hz, 1H), 4.83 (bs, 2H), 2.07 (s, 3H). MS (m/z) (M+1)+: 361.1.

Workup

temperatureThe reaction vessel is chilled in an ice-water bath
extractionThe organic layer is extracted with EtOAc (3×50 mL)
washwashed with brine (1×50 mL)
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-bcd29088c51b41c1b2c058f56df41e21
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293757B2

Reaction notes

Loading…