(2-Aminopyrimidin-5-yl)boronic acid → 3-(2-(2-aminopyrimidin-5-yl)-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propan-1-ol

HRID 1692660Notes

Reaction equation

HRID 1692660 reaction equation
ClC1N=C2C(N=C(C(O)(C)C)N2)=C(N2CCOCC2)N=1.[Si]([O:28][CH2:29][CH2:30][CH2:31][N:32]1[C:40]([C:41]([OH:44])([CH3:43])[CH3:42])=[N:39][C:38]2[C:33]1=[N:34][C:35](Cl)=[N:36][C:37]=2[N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1)(C(C)(C)C)(C)C.[NH2:52][C:53]1[N:58]=[CH:57][C:56](B(O)O)=[CH:55][N:54]=1>>[NH2:52][C:53]1[N:58]=[CH:57][C:56]([C:35]2[N:34]=[C:33]3[C:38]([N:39]=[C:40]([C:41]([OH:44])([CH3:43])[CH3:42])[N:32]3[CH2:31][CH2:30][CH2:29][OH:28])=[C:37]([N:45]3[CH2:46][CH2:47][O:48][CH2:49][CH2:50]3)[N:36]=2)=[CH:55][N:54]=1

Participants

4

Reactant 3

HCID 17750211(2-Aminopyrimidin-5-yl)boronic acidHCID 866372372-(9-(3-(tert-butyldimethylsilyloxy)propyl)-2-chloro-6-morpholino-9H-purin-8-yl)propan-2-olHCID 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 TBDMS-protected bromopropanol via General Procedure C. Crude intermediate 2-(9-(3-(tert-butyldimethylsilyloxy)propyl)-2-chloro-6-morpholino-9H-purin-8-yl)propan-2-ol was treated with 2-aminopyrimidine-5-boronic acid, pinacol ester via General Procedure A and was purified via reverse phase HPLC to give 36 mg of 105 as a white solid. MS (Q1) 415.2 (M)+.

Workup

  1. customwas purified via reverse phase HPLC

Sources & evidence

ORD record
ord-a86fb37255b742af8a7364abbdd1d0b3
Source dataset
uspto-grants-2012_04
Patent number
US08158624B2

Reaction notes

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