1-Acetoxy-2-bromoethane → 2-(2-chloro-6-morpholino-9H-purin-9-yl)ethyl acetate

HRID 2093425Notes

Reaction equation

HRID 2093425 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:3]=1.[C:17]([O:20][CH2:21][CH2:22]Br)(=[O:19])[CH3:18]>>[C:17]([O:20][CH2:21][CH2:22][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([Cl:1])=[N:3][C:4]=2[N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)(=[O:19])[CH3:18]

Participants

3

Reactant 2

HCID 135641-Acetoxy-2-bromoethaneHCID 32746034-(2-chloro-9H-purin-6-yl)morpholine

Product 1

HCID 580152212-(2-chloro-6-morpholino-9H-purin-9-yl)ethyl acetate

Procedure

4-(2-Chloro-9H-purin-6-yl)morpholine (75 mg) was reacted with 2-bromoethyl acetate via General Procedure C to give 2-(2-chloro-6-morpholino-9H-purin-9-yl)ethyl acetate which 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 59.4 mg of 144 as a white solid. MS (Q1) 342.2 (M)+

Sources & evidence

ORD record
ord-41e4cb4393244dbf897c197df09dfde5
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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