2,4-Dichloro-5-fluoropyrimidine → HCID 68783530, compound

HRID 1968530Notes

Reaction equation

HRID 1968530 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH2:7])[CH:4]=[N:3]1.[NH2:8][C@@H:9]1[C@@H:14]2[CH2:15][C@@H:11]([CH:12]=[CH:13]2)[C@@H:10]1[C:16]([NH2:18])=[O:17].Cl[C:20]1[N:25]=[C:24](Cl)[C:23]([Br:27])=[CH:22][N:21]=1.Cl[C:29]1N=C(Cl)C(F)=CN=1>>[Br:27][C:23]1[C:22]([NH:8][C@@H:9]2[C@@H:14]3[CH2:15][C@@H:11]([CH:12]=[CH:13]3)[C@@H:10]2[C:16]([NH2:18])=[O:17])=[N:21][C:20]([NH:7][C:5]2[CH:4]=[N:3][N:2]([CH2:1][CH3:29])[CH:6]=2)=[N:25][CH:24]=1

Participants

5

Reactant 4

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 47709901-methyl-1H-pyrazol-4-amineHCID 42580098rel-(1R,2R,3S,4S)-3-Aminobicyclo[2.2.1]hept-5-ene-2-carboxamide

Product 1

HCID 68783530HCID 68783530, compound

Procedure

The title compound was prepared as described in Example 1, substituting 1-ethyl-1H-pyrazol-4-amine for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/−)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (400 MHz, DMSO-D6, T=90° C.) ppm 1.36 (t, J=7.32 Hz, 3H) 1.42 (d, J=8.54 Hz, 1H) 2.12 (d, J=8.85 Hz, 1H) 2.55 (d, J=7.93 Hz, 1H) 2.77 (s, 1H) 2.88 (s, 1H) 4.05 (q, J=7.32 Hz, 2H) 4.16 (t, J=7.93 Hz, 1H) 6.21-6.39 (m, 2H) 6.77-6.97 (m, 1H) 7.36-7.54 (m, 3H) 7.70 (s, 1H) 7.91 (s, 1H) 8.68 (s, 1H); MS (ESI(+)) m/e 420 (M+H)+.

Sources & evidence

ORD record
ord-6f75806679d9498cb8d261282516376e
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

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