2-Bromobenzyl bromide → 6-[3(R)-Amino-piperidin-1-yl]-1-(2-bromo-benzyl)-1H-pyrimidine-2,4-dione

HRID 602357Notes

Reaction equation

HRID 602357 reaction equation
ClC1N(CC2C=CC=CC=2C#N)C(=O)NC(=O)C=1.[Br:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Br.C(O)(=O)C1C=CC=CC=1.[NH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][N:40]([C:44]2[N:49](CC3C=CC=CC=3C#N)[C:48](=[O:59])[N:47](C)[C:46](=[O:61])[CH:45]=2)[CH2:39]1>>[NH2:37][C@@H:38]1[CH2:43][CH2:42][CH2:41][N:40]([C:44]2[N:49]([CH2:22][C:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=3[Br:19])[C:48](=[O:59])[NH:47][C:46](=[O:61])[CH:45]=2)[CH2:39]1

Participants

4

Reactant 3

HCID 769652-Bromobenzyl bromideHCID 113574682-((6-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrileHCID 666977522-[[6-(3-Aminopiperidin-1-yl)-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile;benzoic acid

Product 1

HCID 112919016-[3(R)-Amino-piperidin-1-yl]-1-(2-bromo-benzyl)-1H-pyrimidine-2,4-dione

Procedure

The title compound was prepared in two steps. The first step was accomplished using the procedure for the preparation of compound 2, except that 2-bromobenzylbromide was used in the place of α-Bromo-o-tolunitrile. The crude product was then converted to the title compound by the method used in the preparation of compound 4. 1H-NMR (400 MHz, CDCl3-CD3OD 10:1): δ 7.52 (d, J=8.1 Hz, 1H), 7.24 (t, J=7.8 Hz, 1H), 7.10 (t, J=7.8 Hz, 1H), 6.89 (d, J=7.579 Hz, 1H), 5.27 (s, 1H), 4.92-5.04 (ABq, J=34.1, 15.0 Hz, 2H), 3.27 (bd, J=10.4 Hz, 1H), 3.09-3.18 (m, 1H), 2.89 (m, 1H), 2.70 (t, J=10.9 Hz, 1H), 2.48 (t, J=12.0 Hz, 1H), 2.03 (m, 1H), 1.60-1.71 (m, 1H), 1.42-1.53 (m, 2H). MS (ES) [m+H] calc'd for C16H20BrN4O2, 379.1; found, 379.1.

Workup

  1. customThe title compound was prepared in two steps

Sources & evidence

ORD record
ord-bac9aa71e4b94b349cb179555dd3365c
Source dataset
uspto-grants-2011_03
Patent number
US07906523B2

Reaction notes

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