Acetonitrile → {2-[(5-{[5-(3-Chlorophenyl)-6-methoxypyridin-3-yl]methyl}pyrimidin-2-yl)amino]ethyl}dimethylamine

HRID 2271471Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[N:11][C:12]([O:22][CH3:23])=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[CH:14]=2)=[CH:4][N:3]=1.C(#N)C.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH2:31].C(N(C(C)C)C(C)C)C>CCOC(C)=O>[Cl:21][C:17]1[CH:16]=[C:15]([C:13]2[CH:14]=[C:9]([CH2:8][C:5]3[CH:4]=[N:3][C:2]([NH:31][CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])=[N:7][CH:6]=3)[CH:10]=[N:11][C:12]=2[O:22][CH3:23])[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A 5 mL microwave vial was charged with 2-chloro-5-{[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl}pyrimidine (Example 2, 50.00 mg, 0.14 mmol), ACN (1.44 mL), N1,N1-dimethylethane-1,2-diamine (0.03 mL, 0.29 mmol), and N-ethyl-N-isopropylpropan-2-amine (77.13 μL, 0.43 mmol). The vial was sealed, and the reaction mixture was heated at 180° C. for 15 minutes. EtOAc (5 mL) was added to the reaction mixture, and the reaction mixture was extracted with water (3×). The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 0-15% MeOH/DCM) afforded the title compound (15.6 mg, 28%). 1H NMR (400 MHz, DMSO-d6) δ 8.21 (s, 2H), 8.09 (s, 1H), 7.67 (br s, 2H), 7.58 (s, 1H), 7.51-7.34 (m, 2H), 6.79 (br s, 1H), 3.84 (s, 3H), 3.72 (s, 2H), 2.42-2.37 (m, 4H), 2.17 (s, 6H). [M+H]=398.20.

Workup

customThe vial was sealed
extractionthe reaction mixture was extracted with water (3×)
dry with materialThe combined organic layers were dried (Na2SO4)
customthe solvent was removed under reduced pressure
customPurification (FCC, SiO2, 0-15% MeOH/DCM)

Sources & evidence

ORD record: ord-500afa8e9671432fb03f5f28ab2c07e2
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120770B2

Reaction notes

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