4-(2-(butylamino)-5-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)cyclohexanol → HCID 178448860, compound

HRID 920668Notes

Reaction equation

HRID 920668 reaction equation
[CH2:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:13]=[C:12]([C@H:22]3[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]3)[C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4].[CH2:29]([NH:33][C:34]1[N:35]=[CH:36][C:37]2[N:42]([C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=3)[CH2:41][CH:40]([CH:50]3[CH2:55][CH2:54][CH:53]([OH:56])[CH2:52][CH2:51]3)[C:38]=2[N:39]=1)[CH2:30][CH2:31][CH3:32]>CO.[Pd]>[CH2:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:13]=[C:12]([C@@H:22]3[CH2:23][CH2:24][C@H:25]([OH:28])[CH2:26][CH2:27]3)[C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4].[CH2:29]([NH:33][C:34]1[N:35]=[CH:36][C:37]2[N:42]([C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=3)[CH:41]=[C:40]([C@H:50]3[CH2:51][CH2:52][C@H:53]([OH:56])[CH2:54][CH2:55]3)[C:38]=2[N:39]=1)[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 2

HCID 867311604-(2-(butylamino)-5-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)cyclohexanolHCID 178448860HCID 178448860, compound

Product 2

HCID 178448859HCID 178448859, compoundYield 13%HCID 178448860HCID 178448860, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of mixture of trans-4-(2-(butylamino)-5-(4-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)cyclohexanol and 4-(2-(butylamino)-5-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)cyclohexanol (0.035 g, 0.091 mmol) in 5 mL MeOH was added Pd/C (0.004 g, 10 wt %). The mixture was stirred overnight under air. After filter through a plug of celite, the filtrate was concentrated and purified by ISCO to provide cis-4-(2-(butylamino)-5-(4-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)cyclohexanol (0.010 g, 13% over 3 steps) and trans-4-(2-(butylamino)-5-(4-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)cyclohexanol (0.012 g+0.040 g, 52% over 3 steps). Cis-isomer (UNC1861A): 1H NMR (400 MHz, CD3OD) δ 8.47 (s, 1H), 7.55-7.49 (m, 3H), 7.32-7.25 (m, 2H), 4.06-3.99 (m, 1H), 3.43 (t, J=7.1 Hz, 2H), 2.97 (tt, J=10.6, 3.7 Hz, 1H), 2.06-1.96 (m, 2H), 1.93-1.82 (m, 4H), 1.79-1.68 (m, 2H), 1.68-1.59 (m, 2H), 1.49-1.39 (m, 2H), 0.97 (t, J=7.4 Hz, 3H); MS m/z 383.3 [M+H]+. Trans-isomer (UNC1860A): 1H NMR (400 MHz, CD3OD) δ 8.45 (s, 1H), 7.53-7.47 (m, 3H), 7.28 (t, J=8.7 Hz, 2H), 3.69-3.57 (m, 1H), 3.42 (t, J=7.1 Hz, 2H), 2.83 (tt, J=12.4, 3.2 Hz 1H), 2.20-2.13 (m, 2H), 2.11-2.02 (m, 2H), 1.73-1.58 (m, 4H), 1.53-1.39 (m, 4H), 0.98 (t, J=7.4 Hz, 3H); MS m/z 383.3 [M+H]+.

Workup

  1. filtrationAfter filter through a plug of celite
  2. concentrationthe filtrate was concentrated
  3. custompurified by ISCO

Sources & evidence

ORD record
ord-4ec161a940874f1ebc9e1a0c68968b40
Source dataset
uspto-grants-2016_03
Patent number
US09273056B2

Reaction notes

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