2,4-Dichloro-5-fluoropyrimidine → HCID 22060680, compound

HRID 2277800Notes

Reaction equation

HRID 2277800 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12]([C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)[NH2:17])=[O:13]>>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][C:16]2[CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=[C:14]([C:12]([O:11][CH3:10])=[O:13])[CH:15]=2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 4026781methyl 3-amino-5-(trifluoromethyl)benzoate

Product 1

HCID 22060680HCID 22060680, compound

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-methoxycarbonyl-5-trifluoromethylaniline gave 2-chloro-5-fluoro-N4-(3-methoxycarbonyl-5-trifluoromethylphenyl)-4-pyrimidineamine. 1H NMR (CD3OD): δ 8.60 (s, 1H), 8.43 (s, 1H), 8.20 (d, 1H, J=3 Hz), 7.99 (s, 1H), 3.96 (s, 3H); 19F NMR (CD3OD): −18332, −18374; and −44259; LCMS: purity: 91%; MS (m/e): 350 (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-b4ae5dacc5d94ce6923afa509ae4961b
Source dataset
uspto-grants-2015_09
Patent number
US09133133B2

Reaction notes

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