2-Methoxypyrimidine-5-boronic acid → HCID 178494063, compound

HRID 2103718Notes

Reaction equation

HRID 2103718 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)=[CH:25][N:24]=1.N1C=C(B(O)O)C=N[CH:33]=1>>[N:13]1([C@H:11]2[CH2:10][C@H:9]([C:7]3[S:8][C:4]4[CH:3]=[C:2]([C:26]5[CH:25]=[N:24][C:23]([O:22][CH3:21])=[N:28][CH:27]=5)[CH:20]=[CH:19][C:5]=4[N:6]=3)[CH2:12]2)[CH2:14][CH2:18][CH2:33][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 3

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 178461421HCID 178461421, compound

Product 1

HCID 178494063HCID 178494063, compound

Procedure

The title compound was prepared according to the procedure described in Example 1F, except for substituting the product of Example 71A for the product of Example 1E, and substituting 2-methoxypyrimidine-5-boronic acid (Frontier Scientific, Inc., Logan, Utah, USA) for pyrimidine-5-boronic acid. 1H NMR (500 MHz, CDCl3) δ ppm 8.78 (s, 2H) 8.07 (d, J=8.24 Hz, 1H) 7.98 (d, J=1.83 Hz, 1H) 7.59 (dd, J=8.39, 1.68 Hz, 1H) 4.09 (s, 3H) 3.78-3.86 (m, 1H) 3.33-3.44 (m, 1H) 2.45-2.65 (m, 8H) 1.58-1.75 (m, 8H). MS: (M+H)+=395.

Sources & evidence

ORD record
ord-ae02d5392a33403fa8307b6041cfb5ce
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

Loading…