Toluene → HCID 11576813, compound

HRID 900172Notes

Reaction equation

HRID 900172 reaction equation
C(OC(OCC)C[NH:6][C:7]1[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])=[CH:24][CH:23]=3)[NH:13][C:9]=2[N:10]=[CH:11][N:12]=1)C.[CH:37]([SH:40])([SH:39])[CH3:38].[C:41]1(C)C=CC=C[CH:42]=1>>[CH3:33][N:31]([CH3:32])[CH2:30][CH2:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:14]2[NH:13][C:9]3[N:10]=[CH:11][N:12]=[C:7]([NH:6][CH2:38][CH:37]4[S:40][CH2:42][CH2:41][S:39]4)[C:8]=3[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 336451,1-EthanedithiolHCID 69216026HCID 69216026, compound

Product 1

HCID 11576813HCID 11576813, compound

Procedure

(2,2-Diethoxyethyl)-{6-[4-(2-dimethylamino-ethoxy)-phenyl]-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-amine (Example 33, Step C; 50 mg, 0.12 mmol) was combined with 12 μl ethanedithiol in 5 ml toluene, then the mixture was heated to reflux for 4 h. After that time the mixture was cooled to rt, concentrated and purified by chromatography on silica gel (CH2Cl2:MeOH=95:5) to give the title compound. 1H-NMR (400 MHz, DMSO-d6) δ 2.21 (s, 6H), 2.61 (t, 2H, J=5.73 Hz), 3.16-3.05 (m, 4H), 3.61 (t, 2H, J=6.07 Hz), 4.03 (t, 2H, J=5.77 Hz), 4.68 (t, 1H, J=6.29 Hz), 5.23 (t, 1H, J=5.86 Hz), 6.86 (d, 2H, J=8.84 Hz), 7.25 (d, 2H, J=8.80 Hz), 8.14-7.38 (m, 5H), 8.21 (s, 1H), 12.12 (s, 1H). Mass Spectrum (ESI) m/e=492 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationconcentrated
  4. custompurified by chromatography on silica gel (CH2Cl2:MeOH=95:5)

Sources & evidence

ORD record
ord-89c45028bf4a4a3ab68c6fd454cdfa53
Source dataset
uspto-grants-2008_04
Patent number
US07358250B2

Reaction notes

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