Tert-Butylamine → tert-Butyl-[3-(2-chloro-pyrimidin-4-yl)-benzyl]-amine

HRID 2386509Notes

Reaction equation

HRID 2386509 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=O)[CH:5]=[CH:4][N:3]=1.[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17]>>[C:16]([NH:20][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:9]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 249019653-(2-Chloro-pyrimidin-4-yl)-benzaldehyde2×

Product 1

HCID 86603310tert-Butyl-[3-(2-chloro-pyrimidin-4-yl)-benzyl]-amineYield 97%

Procedure

3-(2-Chloro-pyrimidin-4-yl)-benzaldehyde (intermediate 1) and tert butylamine were coupled by procedure B. The yield was 97%. LC-MS showed the product had the expected M+H+ of 276. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) 8.6 (d, 1H) 8.1 (s, 1H) 7.9 (d, 1H) 7.6 (d, 1H) 7.5 (m, 2H) 1.2 (s, 9H).

Sources & evidence

ORD record
ord-f678f0a02c3e400698aa219c56d9d96b
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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