Imidazole → HCID 86692152, compound

HRID 527931Notes

Reaction equation

HRID 527931 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([N:8]([CH3:31])[C@@H:9]2[CH2:13][CH2:12][N:11]([C:14]3[C:15]4[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:16]=4[N:17]=[CH:18][N:19]=3)[CH2:10]2)=[N:6][CH:7]=1.[NH:32]1[CH:36]=[CH:35][N:34]=[CH:33]1.C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>CN1C(=O)CCC1.O.[Cu]I>[N:32]1([C:2]2[N:3]=[CH:4][C:5]([N:8]([CH3:31])[C@@H:9]3[CH2:13][CH2:12][N:11]([C:14]4[C:15]5[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])[C:16]=5[N:17]=[CH:18][N:19]=4)[CH2:10]3)=[N:6][CH:7]=2)[CH:36]=[CH:35][N:34]=[CH:33]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 86692149HCID 86692149, compound

Product 1

HCID 86692152HCID 86692152, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of (R)-5-bromo-N-methyl-N-(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)pyrazin-2-amine (50 mg, 0.0991 mmol), imidazole (14 mg, 0.198 mmol), CuI (9.4 mg, 0.050 mmol), Cs2CO3 (32 mg, 0.0991 mmol), and 1,10-phenanthroline (9 mg, 0.050 mmol), in NMP (2 mL) was stirred at 180° C. for 45 minutes in a microwave reactor. It was then cooled to the ambient temperature and diluted with H2O, extracted with EtOAc, washed with brine, dried, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the title compound (20 mg, 41%).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4cce4d6de83b449baf3ba342adec8744
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

Loading…