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

HRID 243317Notes

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[CH:28]=[CH:27][S:26][C:22]=2[N:23]=[CH:24][N:25]=1.C(N(C(C)C)C(C)C)C>C(O)CCC>[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]([NH:18][C:20]2[C:21]3[CH:28]=[CH:27][S:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH3:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Into a 10-mL sealed tube was placed (1S)-1-(1-phenyl-1H-1,3-benzodiazol-2-yl)ethan-1-amine from Example 4 (300 mg, 1.26 mmol, 1.00 equiv), 4-chlorothieno[2,3-d]pyrimidine (250 mg, 1.47 mmol, 1.16 equiv), N-ethyl-N-isopropylpropan-2-amine (322 mg) and BuOH (5 mL). The resulting solution was stirred for 1 overnight at 120° C. and concentrated under vacuum. The residue was applied onto a silica gel column eluted with ethyl acetate/petroleum ether (0:100-80:20) to afford 260 mg (55%) of 143 as a light yellow solid. LC-MS (ES, m/z): 372 [M+H]+. 1H-NMR (300 MHz, CD3OD, ppm): δ 8.19 (s, 1H), 7.70 (d, 1H), 7.68-7.08 (m, 10H), 5.74-5.67 (m, 1H), 1.73 (d, 3H)

Workup

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

Sources & evidence

ORD record: ord-5fbe3b6bee2347b2839de1857d82dec7
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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