4-(2-(4-amino-2-methylphenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine → N-(5-cyclohexyl-2-(methyloxy)phenyl)-N'-(3-methyl-4-((3-(2-(methylamino)-4-pyrimidinyl)-2-pyridinyl)oxy)phenyl)urea

HRID 1361678Notes

Reaction equation

HRID 1361678 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([N:15]=[C:16]=[O:17])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:18][C:19]1[CH:39]=[CH:38][C:22]([O:23][C:24]2[C:29]([C:30]3[CH:35]=[CH:34][N:33]=[C:32]([NH:36][CH3:37])[N:31]=3)=[CH:28][CH:27]=[CH:26][N:25]=2)=[C:21]([CH3:40])[CH:20]=1>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([NH:15][C:16]([NH:18][C:19]3[CH:39]=[CH:38][C:22]([O:23][C:24]4[C:29]([C:30]5[CH:35]=[CH:34][N:33]=[C:32]([NH:36][CH3:37])[N:31]=5)=[CH:28][CH:27]=[CH:26][N:25]=4)=[C:21]([CH3:40])[CH:20]=3)=[O:17])[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 469295424-(2-(4-amino-2-methylphenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amineHCID 83918541HCID 83918541, compound

Product 1

HCID 58588072N-(5-cyclohexyl-2-(methyloxy)phenyl)-N'-(3-methyl-4-((3-(2-(methylamino)-4-pyrimidinyl)-2-pyridinyl)oxy)phenyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 4-cyclohexyl-2-isocyanato-1-methoxy-benzene (56 mg, 0.24 mmol) in toluene (3.0 mL) was added {4-[2-(4-amino-2-methyl-phenoxy)-pyridin-3-yl]-pyrimidin-2-yl}-methyl-amine (46 mg, 0.15 mmol). The mixture was stirred overnight at RT, concentrated and purified by preparative TLC (50% EtOAc/CH2Cl2) to yield N-(5-cyclohexyl-2-(methyloxy)phenyl)-N′-(3-methyl-4-((3-(2-(methylamino)-4-pyrimidinyl)-2-pyridinyl)oxy)phenyl)urea. MS m/z=539 [M+1]+. Calc'd for C31H34N6O3: 538.66.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative TLC (50% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-63691ff1d9b6413db7bc234d2e82270f
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

Loading…