1-{3-[(1-Methylpiperidin-3-yl)oxy]phenyl}methanamine → 6-(4-Chlorophenyl)-3-{3-[(1-methylpiperidin-3-yl)oxy]benzyl}thieno[3,2-d]pyrimidin-4(3H)-one

HRID 2239341Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([O:15]C)=O)=[C:10](/[N:17]=[CH:18]/[N:19]([CH3:21])C)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][CH2:26][CH:25]([O:29][C:30]2[CH:31]=[C:32](CN)[CH:33]=[CH:34][CH:35]=2)[CH2:24]1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]3[C:13](=[O:15])[N:19]([CH2:21][C:34]4[CH:33]=[CH:32][CH:31]=[C:30]([O:29][CH:25]5[CH2:26][CH2:27][CH2:28][N:23]([CH3:22])[CH2:24]5)[CH:35]=4)[CH:18]=[N:17][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (180 mg, 0.558 mmol) and 1-{3-[(1-methylpiperidin-3-yl)oxy]phenyl}methanamine (135 mg, 0.613 mmol) were dissolved in MeOH (2 ml). The reaction was heated in a microwave at 120° C. for 15 minutes, MeOH added, the resulting precipitate filtered and washed with MeOH to yield the title compound as a white solid. Yield: 140 mg (54%). 1H NMR (400 MHz, d6-DMSO) δ 8.66 (s, 1H), 7.92-7.87 (m, 3H), 7.57 (m, 2H), 7.25 (t, 1H, J=8.0 Hz), 6.94 (m, 1H), 6.89 (m, 2H), 5.18 (s, 2H), 4.36 (m, 1H J=4.3 Hz), 3.30 (d, 1H, J=9.6 Hz), 2.81 (d, 1H, J=10.7 Hz), 2.15 (s, 3H), 2.04-1.88 (m, 3H), 1.73-1.67 (m, 1H), 1.57-1.45 (m, 1H), 1.36-1.25 (m, 1H). MS (ESI+) 465.93 (M+1H+).

Workup

filtrationthe resulting precipitate filtered
washwashed with MeOH

Sources & evidence

ORD record: ord-17d49be24e584f708e28d55a5de70a25
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723331B2

Reaction notes

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