(2,4-Dimethoxypyrimidin-5-yl)boronic acid → HCID 178494066, compound

HRID 2047512Notes

Reaction equation

HRID 2047512 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][O:22][C:23]1[N:28]=[CH:27][C:26](B(O)O)=[C:25]([O:32][CH3:33])[N:24]=1.N1C=C(B(O)O)C=NC=1>>[CH3:21][O:22][C:23]1[N:24]=[C:25]([O:32][CH3:33])[C:26]([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[CH3:18])[CH2:10]4)[S:8][C:4]=3[CH:3]=2)=[CH:27][N:28]=1

Participants

4

Reactant 3

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 178461421HCID 178461421, compound

Product 1

HCID 178494066HCID 178494066, compound

Procedure

The title compound was prepared according to the procedure described in Example 1F, substituting the product of Example 11A for the product of Example 1E and substituting 2,6-dimethoxy-5-pyrimidineboronic acid for pyrimidine-5-boronic acid. 1H NMR (500 MHz, CDCl3) δ ppm 8.32 (s, 1H) 8.02 (d, J=8.54 Hz, 1H) 7.98 (d, J=1.53 Hz, 1H) 7.57 (dd, J=8.39, 1.68 Hz, 1H) 4.06 (s, 3H) 4.05 (s, 3H) 3.83-3.95 (m, 1H) 3.51-3.72 (m, 1H) 3.10-3.29 (m, 1H) 2.68-2.80 (m, 3H) 2.40-2.65 (m, 3H) 1.49-2.13 (m, 4H) 1.10-1.27 (s, 3H). MS: (M+H)+=411.

Sources & evidence

ORD record
ord-00bf015ecbb64f6f9a4f2dfca5c9e138
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

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