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

Participants

Role	Name	HCID	Charge
Reactant	2-Bromobenzyl bromide	HCID 76965	—
Reactant	2-((6-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile	HCID 11357468	—
Reactant	2-[[6-(3-Aminopiperidin-1-yl)-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile;benzoic acid	HCID 66697752	—
Product	6-[3(R)-Amino-piperidin-1-yl]-1-(2-bromo-benzyl)-1H-pyrimidine-2,4-dione	HCID 11291901	—

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07781584B2
Source dataset	uspto-grants-2010_08
ORD ID	ord-e1a2172ce7884e04b8471001e9f954b2
Source note	uspto-grants-2010_08