tert-Butyl 4-[4-(4-fluorophenyl)-2-methyl-5-pyrimidin-4-yl-1H-imidazol-1-yl]piperidine-1-carboxylate → 4-[4-(4-Fluorophenyl)-2-methyl-1-piperidin-4-yl-1H-imidazol-5-yl]pyrimidine

HRID 1896668Notes

Reaction equation

HRID 1896668 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH3:32])[N:11]([CH:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)=[CH:4][CH:3]=1.CNC1N=C(C2N(C3CCNCC3)C=NC=2C2C=CC=CC=2)C=CN=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH3:32])[N:11]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 57461734tert-Butyl 4-[4-(4-fluorophenyl)-2-methyl-5-pyrimidin-4-yl-1H-imidazol-1-yl]piperidine-1-carboxylateHCID 58235131HCID 58235131, compound

Product 1

HCID 574617354-[4-(4-Fluorophenyl)-2-methyl-1-piperidin-4-yl-1H-imidazol-5-yl]pyrimidine

Procedure

The title compound was prepared from tert-butyl 4-[4-(4-fluorophenyl)-2-methyl-5-pyrimidin-4-yl-1H-imidazol-1-yl]piperidine-1-carboxylate (C30) according to the general procedure for the synthesis of N-methyl-4-(4-phenyl-1-piperidin-4-yl-1H-imidazol-5-yl)pyrimidin-2-amine (C26) in Example 12, except in this case the extraction was carried out with dichloromethane. Yield: 35.7 mg, 0.106 mmol, 50%. LCMS m/z 338.5 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.96-2.01 (m, 2H), 2.14-2.24 (m, 3H), 2.61-2.68 (m, 2H), 2.65 (s, 3H), 3.19-3.24 (m, 2H), 4.57 (tt, J=12.3, 3.9 Hz, 1H), 6.96 (dd, J=8.8, 8.8 Hz, 2H), 7.12 (dd, J=5.3, 1.4 Hz, 1H), 7.29 (dd, J=8.9, 5.5 Hz, 2H), 8.55 (d, J=5.3 Hz, 1H), 9.30 (d, J=1.3 Hz, 1H).

Workup

  1. extractionthe extraction

Sources & evidence

ORD record
ord-9ab85a1c6d944b24bba4fffd0f535cf1
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

Loading…