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

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

Reactant 2

HCID 6385Tert-Butylamine

HCID 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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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