2-Methoxypyrimidine-5-boronic acid → HCID 178494057, compound

HRID 2103715Notes

Reaction equation

HRID 2103715 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]4C)[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=NC=1>>[N:13]1([C@H:11]2[CH2:12][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)[CH2:10]2)[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 178494057HCID 178494057, compound

Procedure

The title compound was prepared according to the procedure described in Example 1F, except for substituting the product of Example 61A 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 (300 MHz, CDCl3) δ ppm 8.77 (s, 2H) 8.07 (d, J=8.48 Hz, 1H) 7.97 (d, J=2.03 Hz, 1H) 7.59 (dd, J=8.48, 2.03 Hz, 1H) 4.08 (s, 3H) 3.93-4.06 (m, 1H) 3.18-3.34 (m, 5 H) 2.49-2.61 (m, 1H) 2.34-2.47 (m, 3H) 2.03-2.19 (m, 2H). MS: (M+H)+=353.

Sources & evidence

ORD record
ord-5eca29b45f6c498d86acf67ab19569a2
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

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