Isobutyl iodide → 3-(9-isobutyl-6-morpholino-9H-purin-2-yl)phenol

HRID 2093426Notes

Reaction equation

HRID 2093426 reaction equation
ClC1N=C2C(N=CN2)=C(N2CCOCC2)N=1.ICC(C)C.Cl[C:23]1[N:31]=[C:30]2[C:26]([N:27]=[CH:28][N:29]2[CH2:32][CH:33]([CH3:35])[CH3:34])=[C:25]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[N:24]=1.C(=O)([O-])[O:43][C:44]1[CH:49]=[CH:48][CH:47]=[C:46](B2OC(C)(C)C(C)(C)O2)[C:45]=1C(C)(C)C>>[CH2:32]([N:29]1[CH:28]=[N:27][C:26]2[C:30]1=[N:31][C:23]([C:46]1[CH:45]=[C:44]([OH:43])[CH:49]=[CH:48][CH:47]=1)=[N:24][C:25]=2[N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1)[CH:33]([CH3:35])[CH3:34]

Participants

5

Reactant 4

HCID 10556Isobutyl iodideHCID 32746034-(2-chloro-9H-purin-6-yl)morpholineHCID 53421896[2-Tert-butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl] carbonateHCID 580152192-Chloro-9-isobutyl-6-morpholin-4-yl-9H-purine

Product 1

HCID 445441093-(9-isobutyl-6-morpholino-9H-purin-2-yl)phenol

Procedure

4-(2-Chloro-9H-purin-6-yl)morpholine (75 mg) was reacted with 1-iodo-2-methylpropane via General Procedure C. 4-(2-Chloro-9-isobutyl-9H-purin-6-yl)morpholine was reacted with 150 mg tert-butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl carbonate via General Procedure A and purified via reverse phase HPLC to give 62.6 mg of 145 as a white solid. MS (Q1) 354.2 (M)+

Workup

  1. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-03d49c1b95dc43f7ac8d7913fae22afc
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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