Methylamine → 2-(2-(3-hydroxyphenyl)-6-morpholino-9H-purin-9-yl)-N-methylacetamide

HRID 2093422Notes

Reaction equation

HRID 2093422 reaction equation
Cl[C:2]1N=C2C(N=CN2)=C(N2CCOCC2)[N:3]=1.BrCC(OC)=O.ClC1N=C2C(N=CN2CC(OC)=O)=C(N2CCOCC2)N=1.C(=O)([O-])OC1C=CC=C(B2OC(C)(C)C(C)(C)O2)C=1C(C)(C)C.[OH:67][C:68]1[CH:69]=[C:70]([C:74]2[N:82]=[C:81]3[C:77]([N:78]=[CH:79][N:80]3[CH2:83][C:84](O)=[O:85])=[C:76]([N:87]3[CH2:92][CH2:91][O:90][CH2:89][CH2:88]3)[N:75]=2)[CH:71]=[CH:72][CH:73]=1.CN>>[OH:67][C:68]1[CH:69]=[C:70]([C:74]2[N:82]=[C:81]3[C:77]([N:78]=[CH:79][N:80]3[CH2:83][C:84]([NH:3][CH3:2])=[O:85])=[C:76]([N:87]3[CH2:92][CH2:91][O:90][CH2:89][CH2:88]3)[N:75]=2)[CH:71]=[CH:72][CH:73]=1

Participants

7

Reactant 6

HCID 6329MethylamineHCID 60984Methyl bromoacetateHCID 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 58015228Methyl 2-(2-chloro-6-morpholino-9H-purin-9-yl)acetateHCID 669098142-(2-(3-hydroxyphenyl)-6-morpholino-9H-purin-9-yl)acetic acid

Product 1

HCID 445439882-(2-(3-hydroxyphenyl)-6-morpholino-9H-purin-9-yl)-N-methylacetamideYield 10.8%

Procedure

4-(2-Chloro-9H-purin-6-yl)morpholine (75 mg) was reacted with methyl 2-bromoacetate via General Procedure C. Methyl 2-(2-chloro-6-morpholino-9H-purin-9-yl)acetate 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. Crude 2-(2-(3-hydroxyphenyl)-6-morpholino-9H-purin-9-yl)acetic acid (50 mg) was reacted with methylamine via General Procedure F and purified via reverse phase HPLC to give 5.6 mg of 140 as a white solid. MS (Q1) 369.2 (M)+

Workup

  1. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-c83f1190af2a45ef85330bb708724d27
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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