4,5-Dibromo-2-phenylpyrimidine → HCID 50943139, compound

HRID 1484842Notes

Reaction equation

HRID 1484842 reaction equation
Br[C:2]1[C:7]([Br:8])=[CH:6][N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[CH:15]1([C:18]2[CH:22]=[C:21]([NH2:23])[NH:20][N:19]=2)[CH2:17][CH2:16]1>CCCCO>[Br:8][C:7]1[C:2]([NH:23][C:21]2[CH:22]=[C:18]([CH:15]3[CH2:17][CH2:16]3)[NH:19][N:20]=2)=[N:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 581693934,5-Dibromo-2-phenylpyrimidineHCID 178507266HCID 178507266, compound

Product 1

HCID 50943139HCID 50943139, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4,5-dibromo-2-phenylpyrimidine (0.82 g, 3.29 mmol, 1.0 eq) in n-BuOH (20 mL), 3-cyclopropyl-1H-pyrazol-5-amine (0.811 g, 6.58 mmol, 2 equiv.) was added and the reaction mixture was heated to 90° C. for 24 hours, filtered to produce 5-Bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenylpyrimidin-4-amine (Compound 8) (0.75 g, 64.1%). LC-MS (m/z): 357.2 [M+H]+. 1H NMR (300 MHz, DMSO-d6): δ 0.74-0.77 (m, 2H), 0.98-1.02 (m, 2H), 1.96-2.01 (m, 1H), 6.40 (s, 2H), 7.50-7.54 (m, 3H), 8.27-8.30 (m, 2H), 8.63 (s, 1H), 8.88 (s, 2H), 12.32 (s, 1H).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-9784b26ad3ff495ab5482a97597e6264
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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