5-Bromo-2-cyclopropylpyrimidine → (3S)-N,N-dibenzyl-5-(2-cyclopropylpyrimidin-5-yl)chroman-3-amine

HRID 1099411Notes

Reaction equation

HRID 1099411 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]([CH:42]2[CH2:44][CH2:43]2)=[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:37]=[N:38][C:39]([CH:42]3[CH2:44][CH2:43]3)=[N:40][CH:41]=2)[O:11][CH2:10]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 204444135-Bromo-2-cyclopropylpyrimidineHCID 25114260(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine

Product 1

HCID 25115368(3S)-N,N-dibenzyl-5-(2-cyclopropylpyrimidin-5-yl)chroman-3-amineYield 53%

Procedure

The title compound was synthesized as described for Intermediate example I-28 in 53% 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-2-cyclopropylpyrimidine (1.1 equiv); 1H NMR (400 MHz, CDCl3) δ ppm 8.55 (s, 2 H), 7.27-7.36 (m, 8 H), 7.13-7.26 (m, 3 H), 6.86 (dd, 1 H), 6.75 (dd, 1 H), 4.32-4.41 (m, 1 H), 4.02 (t, 1 H), 3.70 (s, 4 H), 3.14-3.25 (m, 1 H), 2.76-2.89 (m, 1 H), 2.59-2.69 (m, 1 H), 2.30-2.40 (m, 1 H), 1.22-1.28 (m, 2 H), 1.13-1.21 (m, 2 H); MS (ESI) m/z 448[M+H+].

Sources & evidence

ORD record
ord-849789b63960455a8d35bd0ac255c49d
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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