4-Hexyloxyaniline → HCID 22060236, compound

HRID 2277796Notes

Reaction equation

HRID 2277796 reaction equation
[Cl:1][C:2]1N=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)[C:5]([F:20])=[CH:4][N:3]=1.ClC1N=C(Cl)[C:25](F)=[CH:24]N=1.[CH2:30](OC1C=CC(N)=CC=1)CCCCC>>[Cl:1][C:2]1[CH:30]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:24][CH3:25])=[CH:11][CH:10]=2)[C:5]([F:20])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 383604-HexyloxyanilineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 220610772-chloro-N4-(4-n-butyloxyphenyl)-5-fluoro-4-pyrimidineamine

Product 1

HCID 22060236HCID 22060236, compound

Procedure

In like manner to the preparartion of 2-chloro-N4-(4-n-butyloxyphenyl)-5-fluoro-4-pyrimidineamine, the reaction of 2,4-dichloro-5-fluoropyrimidine with 4-n-hexyloxyaniline gave 2-chloro-N4-(4-n-hexyloxyphenyl)-5-fluoro-4-pyridineamine. The crude product was purified by chromatography (4:1 CHCl3/EtOAc) to afford (14) (0.74 g, 76%) as a red-brown oil that solidified upon standing: 1H NMR (300 MHz, CDCl3) δ 8.01 (d, J=2.7 Hz, 1H), 7.50 (d, J=9.0 Hz, 2H), 6.92 (d, J=9.0 Hz, 2H), 6.84 (bs, 1H), 3.96 (t, J=6.5 Hz, 2H), 1.83-1.74 (m, 2H), 1.48-1.41 (m, 2H), 1.36-1.34 (m, 4H), 0.93-0.89 (m, 3H).

Sources & evidence

ORD record
ord-20987acef6f84e4da841e6607aff527a
Source dataset
uspto-grants-2015_09
Patent number
US09133133B2

Reaction notes

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