1,3-Benzodioxol-5-amine → 4-(3,4-Methylenedioxyanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 2084123Notes

Reaction equation

HRID 2084123 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[N:3]=1.[CH2:18]1[O:27][C:26]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][C:20]=2[O:19]1>>[CH2:18]1[O:27][C:26]2[CH:25]=[CH:24][C:22]([NH:23][C:2]3[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]4[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=4)[N:3]=3)=[CH:21][C:20]=2[O:19]1

Participants

3

Reactant 2

HCID 843101,3-Benzodioxol-5-amineHCID 14859894-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 99688314-(3,4-Methylenedioxyanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine

Procedure

The title compound was prepared from a mixture of 4-chloro-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 3,4-methylenedioxyaniline (53 mg, 0.386 mmol) similar to Example 58 and isolated as a dark brown solid (47 mg, 68%). 1H NMR (CDCl3): 8.77 (dd, J=1.5, 4.5 Hz, 2H), 8.26 (dd, J=1.5, 4.5 Hz, 2H), 7.06 (s, 1H), 6.93 (s, 1H), 6.89 (d, J=8.1 Hz, 1H), 6.81 (dd, J=2.1, 8.1 Hz, 1H), 6.81 (s, 1H), 6.06 (s, 2H).

Sources & evidence

ORD record
ord-eb131410ffca4413bee648e6746328e7
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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