Sodium Carbonate → [4-Chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-yl]-methyl-amine

HRID 28580

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:22][CH3:23])=[C:16](B(O)O)[CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(O)C(O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:6]1[CH:7]=[C:2]([C:14]2[CH:13]=[C:12]([Cl:11])[CH:17]=[CH:16][C:15]=2[O:21][CH2:22][CH3:23])[N:3]=[C:4]([NH:9][CH3:10])[N:5]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To an argon saturated solution of N-(4,6-dichloro-pyrimidin-2-yl)-methyl-amine (200 mg, 1.1 mmol), 5-chloro-2-ethoxy-phenylboronic acid (248 mg, 1.21 mmol) and palladium acetate (38 mg, 0.16 mmol) in dimethyl ethylene glycol (20 ml) was added a solution of sodium carbonate (240 mg, 2.2 mmol) in water (5 ml) followed by triphenylphosphine (66 mg, 0.33 mmol). After stirring at 70° C. under an argon atmosphere for 60 hours, the mixture was filtered through a pad of celite under suction and the filtrate was dried over magnesium sulfate. Evaporation of the solvent under reduced pressure provided [4-chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-yl]-methyl-amine (300 mg, 90% yield).

Workup

filtrationthe mixture was filtered through a pad of celite under suction
dry with materialthe filtrate was dried over magnesium sulfate
customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-092e9e7a5b8a433aa456fb1bf7873c0d
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419984B2

Linked notes

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