2,4-Dichloro-5-fluoropyrimidine → HCID 68780804, compound

HRID 1968540Notes

Reaction equation

HRID 1968540 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[C:4]([CH3:29])=[N:3][N:2]([CH3:1])[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 42580098105786-40-1

Product 1

HCID 68780804HCID 68780804, compound

Procedure

The title compound was prepared as described in Example 1, substituting 1,3-dimethyl-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) ppm 1.37-1.43 (m, 1H) 2.05-2.17 (m, 4H) 2.49-2.53 (m, 1H) 2.72 (s, 1H) 2.86 (s, 1H) 3.70 (s, 3H) 4.03-4.14 (m, 1H) 6.20 (dd, J=5.80, 3.05 Hz, 1H) 6.30 (dd, J=5.65, 2.90 Hz, 1H) 7.38 (d, J=7.93 Hz, 1H) 7.64 (s, 1H) 7.88 (s, 1H) 7.91 (s, 1H); MS (ESI(+)) m/e 418, 420 (M+H)+.

Sources & evidence

ORD record
ord-fedd3b9ff2ca4ea8b7cf3f9707954a8f
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

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