Toluene → 4-(3-Morpholinophenyl)-N-(4-(3-vinyl-1H-1,2,4-triazol-1-yl)phenyl)pyrimidin-2-amine

HRID 40741Notes

Reaction equation

Br[C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)[CH:21]=4)[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[N:3]=1.[CH2:32]([Sn](CCCC)(CCCC)C=C)[CH2:33]CC.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[O:29]1[CH2:30][CH2:31][N:26]([C:22]2[CH:21]=[C:20]([C:18]3[CH:17]=[CH:16][N:15]=[C:14]([NH:13][C:10]4[CH:11]=[CH:12][C:7]([N:4]5[CH:5]=[N:6][C:2]([CH:32]=[CH2:33])=[N:3]5)=[CH:8][CH:9]=4)[N:19]=3)[CH:25]=[CH:24][CH:23]=2)[CH2:27][CH2:28]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-(4-(3-bromo-1H-1,2,4-triazol-1-yl)phenyl)-4-(3-morpholinophenyl)pyrimidin-2-amine (0.024 g, 0.05 mmol), tributyl(vinyl)stannane (0.032 g, 0.10 mmol), Pd(PPh3)4 (0.012 g, 0.01 mmol), toluene (0.4 mL) and DMF (0.1 mL) was heated in a sealed tube at 120° C. with microwave irradiation for 1 h. The reaction mixture was cooled down to room temperature. Purification of this material by column chromatography on silica gel (40% EtOAc/hexane) provided the desired product as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.43 (d, 1H), 8.36 (s, 1H), 7.80 (d, 2H), 7.59 (d, 2H), 7.37 (m, 4H), 7.14 (d, 1H), 7.01 (dd, 1H), 6.75 (dd, 1H), 6.27 (d, 1H), 5.51 (d, 1H), 3.84 (m, 4H), 3.20 (m, 4H). MS (ESI) 426.29 (M+H).

Workup

temperatureThe reaction mixture was cooled down to room temperature
customPurification of this material by column chromatography on silica gel (40% EtOAc/hexane)

Sources & evidence

ORD record: ord-7191db7aa4da4eed8d966097db58341e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530480B2

Reaction notes

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