Diisopropylethylamine → (S)-5-methyl-N-(1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 243318Notes

Reaction equation

[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:16]([NH2:18])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:20]1[C:21]2[C:28]([CH3:29])=[CH:27][NH:26][C:22]=2[N:23]=[CH:24][N:25]=1.C(N(C(C)C)C(C)C)C>C(O)CCC>[CH3:29][C:28]1[C:21]2[C:20]([NH:18][C@H:16]([C:8]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=3)[CH3:17])=[N:25][CH:24]=[N:23][C:22]=2[NH:26][CH:27]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Into a 10-mL sealed tube was placed (S)-1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethanamine from Example 4 (300 mg, 1.26 mmol, 1.00 equiv), 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (250 mg, 1.49 mmol, 1.18 equiv), N-ethyl-N-isopropylpropan-2-amine (322 mg, 2.50 mmol, 1.97 equiv) and BuOH (5 mL). The resulting solution was stirred for overnight at 120° C. and concentrated under vacuum. The residue was applied onto a silica gel column eluted with ethyl acetate/hexane (0:100-80:20) to afford 270 mg (58%) of 144 as a white solid. LC-MS (ES, m/z): 369 [M+H]+. H-NMR (300 MHz, CD3OD, ppm): δ 7.98 (s, 1H), 7.70-7.53 (m, 6H), 7.33-7.23 (m, 2H), 7.14-7.11 (m, 1H), 6.83 (d, 1H), 5.68-5.61 (m, 1H), 2.49 (d, 3H), 1.67 (d, 3H)

Workup

customInto a 10-mL sealed tube
concentrationconcentrated under vacuum
washeluted with ethyl acetate/hexane (0:100-80:20)

Sources & evidence

ORD record: ord-747c0bc796f14553a1f45c36bf3d8889
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

Loading…