(Pyrimidin-5-yl)boronic acid → HCID 178423691, compound

HRID 2103711Notes

Reaction equation

HRID 2103711 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([C@H:9]3[CH2:12][C@H:11]([N:13]4[CH2:17][CH2:16][CH2:15][C@H:14]4[CH3:18])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:21][C:22]1[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=[C:24]([CH3:37])[N:23]=1.N1C=C(B(O)[OH:45])C=NC=1>>[CH3:21][C:22]1[C:27]([C:2]2[CH:20]=[CH:19][C:5]3[N:6]=[C:7]([C@H:9]4[CH2:12][C@H:11]([N:13]5[CH2:17][CH2:16][CH2:15][C@H:14]5[CH2:18][OH:45])[CH2:10]4)[S:8][C:4]=3[CH:3]=2)=[CH:26][CH:25]=[C:24]([CH3:37])[N:23]=1

Participants

4

Reactant 3

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 219800342,6-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 178461421HCID 178461421, compound

Product 1

HCID 178423691HCID 178423691, compound

Procedure

The title compound was prepared according to the procedure described in Example 1F, substituting the product of Example 74A for the product of Example 1E and substituting the product of Example 2A for pyrimidine-5-boronic acid. 1H NMR (300 MHz, CDCl3) δ ppm 8.02 (d, J=8.81 Hz, 1H) 7.77 (d, J=1.36 Hz, 1H) 7.45 (d, J=7.80 Hz, 1H) 7.40 (dd, J=8.48, 1.70 Hz, 1H) 7.07 (d, J=7.80 Hz, 1H) 3.83-4.00 (m, 1H) 3.52-3.75 (m, 2H) 3.32-3.47 (m, 1H) 2.99-3.17 (m, 1H) 2.63-2.80 (m, 3H) 2.59 (s, 3H) 2.50 (s, 3H) 1.70-2.08 (m, 5H) 1.46-1.65 (m, 2H). MS: (M+H)+=394.

Sources & evidence

ORD record
ord-c0ab35a0e4004fc4bd859796d4b47a3f
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

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