Sodium Carbonate → 3-cyclopropyl-N-((2,4-dimethoxy-6-vinylpyrimidin-5-yl)methyl)-1-ethyl-1H-pyrazol-5-amine

HRID 80859

Reaction equation

HRID 80859 reaction equation
Cl[C:2]1[C:7]([CH2:8][NH:9][C:10]2[N:14]([CH2:15][CH3:16])[N:13]=[C:12]([CH:17]3[CH2:19][CH2:18]3)[CH:11]=2)=[C:6]([O:20][CH3:21])[N:5]=[C:4]([O:22][CH3:23])[N:3]=1.[CH3:24][C:25]1(C)C(C)(C)OB(C=C)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:17]1([C:12]2[CH:11]=[C:10]([NH:9][CH2:8][C:7]3[C:6]([O:20][CH3:21])=[N:5][C:4]([O:22][CH3:23])=[N:3][C:2]=3[CH:24]=[CH2:25])[N:14]([CH2:15][CH3:16])[N:13]=2)[CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86690292N-((4-chloro-2,6-dimethoxypyrimidin-5-yl)methyl)-3-cyclopropyl-1-ethyl-1H-pyrazol-5-amine

Product 1

HCID 866902933-cyclopropyl-N-((2,4-dimethoxy-6-vinylpyrimidin-5-yl)methyl)-1-ethyl-1H-pyrazol-5-amine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of N-((4-chloro-2,6-dimethoxypyrimidin-5-yl)methyl)-3-cyclopropyl-1-ethyl-1H-pyrazol-5-amine (2.42 g, 7.16 mmol) in DME (50 mL) and water (15 mL) was added 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (2.5 mL, 14.3 mmol), Pd(Ph3P)4 (0.828 g, 0.716 mmol) and sodium carbonate (2.47 g, 23.3 mmol). The mixture was sparged with argon for 15 min and then heated at reflux for 18 h. The mixture was then absorbed onto silica gel and dried under reduced pressure. After dry loading, the product was purified by FCC (10-75% EtOAc/heptane) to give 3-cyclopropyl-N-((2,4-dimethoxy-6-vinylpyrimidin-5-yl)methyl)-1-ethyl-1H-pyrazol-5-amine. MS (ESI+) m/z 330.1 (M+H)+.

Workup

  1. customThe mixture was sparged with argon for 15 min
  2. temperatureheated
  3. temperatureat reflux for 18 h
  4. customThe mixture was then absorbed onto silica gel
  5. customdried under reduced pressure
  6. customAfter dry loading
  7. customthe product was purified by FCC (10-75% EtOAc/heptane)

Sources & evidence

ORD record
ord-0c2d60243c7b4d8db4b4634857a6857c
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Linked notes

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