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

HRID 14907

Reaction equation

HRID 14907 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-4b4178151fca419dac819ae8ff154559
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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