Boronic Acid → 2-Cyclopropylpyrimidine-4-boronic Acid

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]2[CH2:10][CH2:9]2)[N:3]=1.[BH:11]([OH:13])[OH:12].O1BOBOB1>>[CH:8]1([C:4]2[N:3]=[C:2]([B:11]([OH:13])[OH:12])[CH:7]=[CH:6][N:5]=2)[CH2:10][CH2:9]1

Participants

Reactant 3

HCID 61668Boronic Acid

HCID 1361341,3,5,2,4,6-Trioxatriborinane

HCID 457875764-Bromo-2-cyclopropylpyrimidine

Product 1

HCID 667347612-Cyclopropylpyrimidine-4-boronic AcidYield 90%

Procedure

The title compound was prepared from 4-bromo-2-cyclopropylpyrimidine (WO 00/066566) in 90% yield (25 mmol scale) following the procedure by Li et al. (J. Org. Chem. 2002, 67, 5394-5397). LC-MS suggested that the product was composed of the boronic acid and the trimeric anhydride (sym-boroxine).

Sources & evidence

ORD record: ord-29e1a31173c749d7ab55e28fa1292af5
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655664B2

Reaction notes

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