(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine → 5-[(3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl]-N,N-dimethylpyrimidine-2-carboxamide

HRID 1099413Notes

Reaction equation

HRID 1099413 reaction equation
[CH2:1]([N:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2B2OC(C)(C)C(C)(C)O2)[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:36]1[CH:37]=[N:38][C:39]([C:42]([N:44]([CH3:46])[CH3:45])=[O:43])=[N:40][CH:41]=1>>[CH2:28]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[C:36]2[CH:41]=[N:40][C:39]([C:42]([N:44]([CH3:46])[CH3:45])=[O:43])=[N:38][CH:37]=2)[O:11][CH2:10]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 25114260(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amineHCID 595599905-bromo-N,N-dimethylpyrimidine-2-carboxamide

Product 1

HCID 251155945-[(3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl]-N,N-dimethylpyrimidine-2-carboxamideYield 61%

Procedure

The title compound was synthesized as described for Intermediate example I-28 in 61% yield starting from (3S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl)chroman-3-amine and 5-bromo-N,N-dimethylpyrimidine-2-carboxamide. The reaction mixture was irradiated in a microwave at 140° C. for 20 min; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.92 (s, 2 H), 7.23-7.34 (m, 8 H), 7.15-7.22 (m, 3 H), 6.84-6.93 (m, 2 H), 4.31-4.39 (m, 1 H), 4.05 (t, 1 H), 3.60-3.76 (m, 4 H), 3.08-3.15 (m, 1 H), 3.06 (s, 3 H), 2.94-3.05 (m, 1 H), 2.88 (s, 3 H), 2.52-2.59 (m, 1 H); MS (ESI) m/z 452[M+H+].

Workup

  1. customThe reaction mixture was irradiated in a microwave at 140° C. for 20 min

Sources & evidence

ORD record
ord-94558c55c1bf4b9eb3aecb3576e9425f
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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