Cesium carbonate → 4-(2-(4-amino-2-methylphenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine

HRID 1361677Notes

Reaction equation

HRID 1361677 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:17]1[C:22]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH3:30])[N:24]=2)=[CH:21][CH:20]=[CH:19][N:18]=1>CN1C(=O)CCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:17]2[C:22]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH3:30])[N:24]=3)=[CH:21][CH:20]=[CH:19][N:18]=2)=[C:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 760815-Amino-2-hydroxytolueneHCID 161090044-(2-chloro-3-pyridinyl)-N-methyl-2-pyrimidinamine

Product 1

HCID 469295424-(2-(4-amino-2-methylphenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

4-Amino-2-methyl-phenol (84 mg, 0.68 mmol), Cs2CO3 (665 mg, 2.04 mmol) and NMP (2.5 mL) were combined. The mixture was heated for 5 minutes at 100° C., cooled to RT and [4-(2-chloro-pyridin-3-yl)-pyrimidin-2-yl]-methyl-amine (150 mg, 0.68 mmol) was added. The mixture was heated in the microwave to 210° C. for 20 minutes, cooled, filtered through a plug of cotton and purified by reverse-phase HPLC (Gilson, acidic mobile phase) to yield the title compound. MS m/z=308 [M+1]+. Calc'd for C17H17N5O: 307.36.

Workup

  1. temperaturecooled to RT
  2. temperatureThe mixture was heated in the microwave to 210° C. for 20 minutes
  3. temperaturecooled
  4. filtrationfiltered through a plug of cotton
  5. custompurified by reverse-phase HPLC (Gilson, acidic mobile phase)

Sources & evidence

ORD record
ord-30aa7e8e9d1f468cad1cb0a6438a3851
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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