1-Acetoxy-2-bromoethane → 3-(2-(2-aminopyrimidin-5-yl)-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propan-1-ol

HRID 2093392Notes

Reaction equation

HRID 2093392 reaction equation
ClC1N=C2C(N=C([C:11]([OH:14])(C)C)N2)=C(N2CCOCC2)N=1.C(OCCBr)(=O)C.C(O[CH2:32][CH2:33][N:34]1[C:42]([C:43]([OH:46])([CH3:45])[CH3:44])=[N:41][C:40]2[C:35]1=[N:36][C:37](Cl)=[N:38][C:39]=2[N:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1)(=O)C.[NH2:54][C:55]1[N:60]=[CH:59][C:58](B(O)O)=[CH:57][N:56]=1>>[NH2:54][C:55]1[N:60]=[CH:59][C:58]([C:37]2[N:36]=[C:35]3[C:40]([N:41]=[C:42]([C:43]([OH:46])([CH3:45])[CH3:44])[N:34]3[CH2:33][CH2:32][CH2:11][OH:14])=[C:39]([N:47]3[CH2:48][CH2:49][O:50][CH2:51][CH2:52]3)[N:38]=2)=[CH:57][N:56]=1

Participants

5

Reactant 4

HCID 135641-Acetoxy-2-bromoethaneHCID 17750211(2-Aminopyrimidin-5-yl)boronic acidHCID 580152242-(2-Chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)ethyl acetateHCID 178458928HCID 178458928, compound

Product 1

HCID 445450423-(2-(2-aminopyrimidin-5-yl)-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propan-1-ol

Procedure

100 mg of 2-(2-chloro-6-morpholino-9H-purin-8-yl)propan-2-ol was treated with 2-bromoethyl acetate via General Procedure C. Crude intermediate 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)ethyl acetate was treated with 2-aminopyrimidine-5-boronic acid, pinacol ester via General Procedure A and was purified via reverse phase HPLC to give 54 mg of 106 as a white solid. MS (Q1) 401.2 (M)+.

Workup

  1. customwas purified via reverse phase HPLC

Sources & evidence

ORD record
ord-f0a45f0abf434fc8b969f7586525e5cc
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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