(Pyrimidin-5-yl)boronic acid → HCID 25115138, compound

HRID 1099409Notes

Reaction equation

[N:1]1[CH:6]=[C:5](B(O)O)[CH:4]=[N:3][CH:2]=1.FC(F)(F)S(O[C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH2:18][C@H:19]([N:26]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:20][O:21]2)(=O)=O>>[CH2:34]([N:26]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@H:19]1[CH2:18][C:17]2[C:22](=[CH:23][CH:24]=[CH:25][C:16]=2[C:5]2[CH:6]=[N:1][CH:2]=[N:3][CH:4]=2)[O:21][CH2:20]1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acid

HCID 25053925(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Product 1

HCID 25115138HCID 25115138, compoundYield 78%

Procedure

The title compound was synthesized as described for Intermediate example I-2 in 78% yield, starting from 5-pyrimidinylboronic acid and (3S)-3-(dibenzylamino)-3,4-dihydro -2H-chromen-5-yl trifluoromethanesulfonate; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.24 (s, 1 H), 8.86 (s, 2 H), 7.24-7.34 (m, 8 H), 7.15-7.23 (m, 3 H), 6.86 (d, 2 H), 4.32-4.38 (m, 1 H), 4.00-4.08 (m, 1 H), 3.61-3.75 (m, 4 H), 3.05-3.14 (m, 1 H), 2.93-3.03 (m, 1 H), 2.46-2.54 (m, 1 H, obscured by DSMO); MS (ESI) m/z 408[M+H+].

Sources & evidence

ORD record: ord-1a9540b1806b4398947c077ad5e1b5c8
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143408B2

Reaction notes

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