2-Methoxypyrimidine-5-boronic acid → HCID 25116059, compound

HRID 1099421Notes

Reaction equation

HRID 1099421 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12](Br)[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][O:28][C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][N:30]=1>>[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([C:32]3[CH:31]=[N:30][C:29]([O:28][CH3:27])=[N:34][CH:33]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 66814092HCID 66814092, compound

Product 1

HCID 25116059HCID 25116059, compoundYield 80%

Procedure

The title compound was synthesized as described for Intermediate example I-4 in 80% yield starting from (S)-N,N-dibenzyl-8-bromo-1,2,3,4-tetrahydronaphthalen-2-amine and 2-methoxypyrimidine-5-boronic acid (1.9 equiv) and. The reaction mixture was irradiated in a microwave under an atmosphere of argon at 140° C. for 1 h; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.59 (s, 2 H), 7.22-7.32 (m, 8 H), 7.09-7.20 (m, 4 H), 7.00-7.04 (m, 1 H), 4.00 (s, 3 H), 3.53-3.70 (m, 4 H), 2.87-3.00 (m, 2 H), 2.64-2.85 (m, 2 H), 2.45-2.54 (m, 1 H, obscured by DMSO), 2.05-2.14 (m, 1 H), 1.62-1.78 (m, 1 H); MS (ESI) m/z 436[M+H+].

Workup

  1. customThe reaction mixture was irradiated in a microwave under an atmosphere of argon at 140° C. for 1 h

Sources & evidence

ORD record
ord-9e3cb6308a7940a1afcea3b68a777207
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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