Imidazole → HCID 59380441, compound

HRID 2353828Notes

Reaction equation

Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]2[C:10]3[C:15]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=5)=[C:19]([Cl:32])[CH:18]=4)=[N:14][CH:13]=[N:12][C:11]=3[S:33][C:6]=2[CH:5]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[NH:42]1[CH:46]=[CH:45][N:44]=[CH:43]1>CN(C=O)C>[Cl:32][C:19]1[CH:18]=[C:17]([NH:16][C:15]2[C:10]3[C:7]4[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][N:42]5[CH:46]=[CH:45][N:44]=[CH:43]5)=[CH:5][C:6]=4[S:33][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:22]=[CH:21][C:20]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 7-(2-bromoethyl)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}[1]benzothieno[2,3-d]pyrimidin-4-amine (40 mg, 0.07 mmol, 1 equiv) in DMF were added sodium iodide (11 mg, 0.07 mmol, 1 equiv), sodium carbonate (16 mg, 0.15 mmol, 2 equiv), and imidazole (10 mg, 0.15 mmol, 2 equiv). The resulting mixture was heated at 80° C. for 14 h. The reaction was cooled to rt and then concentrated in vacuo. The resulting crude material was purified by prep-TLC (10% methanol/DCM) and afforded a yellow solid (17.9 mg, 0.03 mmol, 45%). 1H-NMR (CD3OD) δ 8.40 (s, 1H), 8.24 (d, J=8.3 Hz, 1H), 7.71 (m, 2H), 7.45-7.36 (m, 3H), 7.28 (d, J=8.1 Hz, 2H), 7.23 (d, J=9.6 Hz, 1H), 7.10 (d, J=8.1 Hz, 1H), 7.09 (s, 1H), 7.04 (td, 1H), 6.92 (s, 1H), 5.12 (s, 2H), 4.35 (t, 2H), 3.23 (t, 2H); LCMS RT=3.22 min, [M+H]+=530

Workup

temperatureThe reaction was cooled to rt
concentrationconcentrated in vacuo
customThe resulting crude material was purified by prep-TLC (10% methanol/DCM)

Sources & evidence

ORD record: ord-062e3e137bc34a8d80652275f493be2f
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750017B2

Reaction notes

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