2,4-Dichloro-5-fluoropyrimidine → 2-chloro-N4-(3,4-difluoromethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine

HRID 1990327Notes

Reaction equation

HRID 1990327 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[F:10][C:11]1[C:12]2[O:17][CH2:16][O:15][NH:14][C:13]=2[CH:18]=[CH:19][C:20]=1[F:21]>>[Cl:1][C:2]1[N:7]=[C:6]([NH:14][C:13]2[CH:18]=[C:19]3[O:15][CH2:16][O:17][C:12]=2[C:11]([F:10])=[C:20]3[F:21])[C:5]([F:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 66759615HCID 66759615, compound

Product 1

HCID 220602142-chloro-N4-(3,4-difluoromethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine

Procedure

In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3,4-difluoromethylenedioxyaniline gave 2-chloro-N4-(3,4-difluoromethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.09 (d, 1H, J=3 Hz), 7.70 (d, 1H, J=2.4 Hz), 7.10 (dd, 1H, J=2.4 and 8.7 Hz), 7.06 (t, 1H, J=8.1 Hz), 6.97 (bs, 1H); 19F NMR (CDCl3): −14175 and −44562; LCMS: purity: 95%; MS (m/e): 304 (MH+).

Workup

  1. customIn like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine

Sources & evidence

ORD record
ord-a6c0d55005fc4c00940e02468bbddbe5
Source dataset
uspto-grants-2010_01
Patent number
US07642351B2

Reaction notes

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