2-Methoxypyrimidine-5-boronic acid → (2R)-N,N-dibenzyl-8-(2-methoxypyrimidin-5-yl)-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 1099422Notes

Reaction equation

HRID 1099422 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][N:4]=1.[CH2:12]([N:19]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@@H:20]1[CH2:29][CH2:28][C:27]2[C:22](=[C:23](Br)[CH:24]=[CH:25][CH:26]=2)[CH2:21]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:31]([N:19]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:20]1[CH2:29][CH2:28][C:27]2[C:22](=[C:23]([C:6]3[CH:5]=[N:4][C:3]([O:2][CH3:1])=[N:8][CH:7]=3)[CH:24]=[CH:25][CH:26]=2)[CH2:21]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 22082960(2R)-N,N-dibenzyl-8-bromo-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 25116061(2R)-N,N-dibenzyl-8-(2-methoxypyrimidin-5-yl)-1,2,3,4-tetrahydronaphthalen-2-amineYield 63%

Procedure

The title compound was synthesized as described for Intermediate example I-2 in 63% yield, starting from 2-methoxypyrimidine-5-boronic acid and (2R)-N,N-dibenzyl-8-bromo -1,2,3,4-tetrahydronaphthalen-2-amine. The reaction mixture was irradiated in a microwave at 150° C. for 1 h; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.59 (s, 2 H), 7.21-7.33 (m, 8 H), 7.08-7.21 (m, 4 H), 7.02 (dd, 1 H), 4.00 (s, 3 H), 3.53-3.70 (m, 4 H), 2.87-3.01 (m, 2 H), 2.64-2.84 (m, 2 H), 2.43-2.53 (m, 1 H, obscured by DMSO), 2.03-2.15 (m, 1 H), 1.62-1.77 (m, 1 H); MS (ESI) m/z 436[M+H+].

Workup

  1. customThe reaction mixture was irradiated in a microwave at 150° C. for 1 h

Sources & evidence

ORD record
ord-0d01838f754a479eabe7a9533250370e
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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