Lithium Hydroxide → (Pyrimidin-5-yl)boronic acid

HRID 1045994Notes

Reaction equation

[NH:1]1[CH2:7][C:5](=O)N[C:2]1=O.[Li+].[OH-:9].[O:10]=S(Cl)Cl.CO.[BH4-:16].[Na+].Br[C:19]#[N:20]>>[N:20]1[CH:19]=[C:5]([B:16]([OH:10])[OH:9])[CH:7]=[N:1][CH:2]=1

Participants

Reactant 5

HCID 3939Lithium Hydroxide

HCID 10006Hydantoin

HCID 10476Cyanogen Bromide

HCID 4311764Sodium borohydride

HCID 21881854HCID 21881854, compound

Product 1

HCID 2795193(Pyrimidin-5-yl)boronic acid

Procedure

In a manner similar to that described previously (Example 1, Steps 1-4 and Example 3, Step 4), compound 37G was subjected to the following sequence: hydantoin formation with (NH4)2CO3/KCN, hydrolysis with LiOH, methyl ester formation with SOCl2/MeOH, reduction with NaBH4, and cyclization with BrCN to provide (±)-37H (LCMS m/z 295/297, MH+). Final Suzuki coupling with pyrimidine-5-boronic acid afforded the title compound (±)-37. LCMS m/z 295 (MH+).

Workup

customto provide (±)-37H (LCMS m/z 295/297, MH+)

Sources & evidence

ORD record: ord-cf3ce825b3ac4449ba27aa156303cb73
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569312B2

Reaction notes

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