HCID 58169240, compound → HCID 58169125, compound

HRID 1484897Notes

Reaction equation

HRID 1484897 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([NH2:9])[NH:6][N:5]=2)[CH2:3][CH2:2]1.[Br:10][C:11]1[N:16]=[C:15](Br)[C:14]([C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[CH:13][N:12]=1>CCO>[Br:10][C:11]1[N:16]=[C:15]([NH:9][C:7]2[CH:8]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[NH:5][N:6]=2)[C:14]([C:18]#[C:19][Si:20]([CH3:21])([CH3:23])[CH3:22])=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 58169240HCID 58169240, compoundHCID 178507266HCID 178507266, compound

Product 1

HCID 58169125HCID 58169125, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

(Step 4) A solution of 3-cyclopropyl-1H-pyrazol-5-amine (12.241 g, 99.39 mmol, 1.5 equiv.) in EtOH was added to a solution of compound 2,4-dibromo-5-((trimethylsilyl)ethynyl) pyrimidine (22.136 g, 66.26 mmol,) in EtOH (220 mL) at 20° C. After 12 h, EtOH was evaporated under reduce pressure. The residue was purified by silica-gel column chromatography (mobile phase: petroleum ether/ethyl acetate=20/1˜5/1) to afford solid product 2-Bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-((trimethylsilyl)ethynyl) pyrimidin-4-amine (9.948 g, 40%). LC-MS (m/z)=377.0 [M+H]+.

Workup

  1. customEtOH was evaporated
  2. customThe residue was purified by silica-gel column chromatography (mobile phase: petroleum ether/ethyl acetate=20/1˜5/1)

Sources & evidence

ORD record
ord-ca44f6f7adb840b3acfdeea2fc14804c
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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