Water → HCID 68029370, compound

HRID 527942Notes

Reaction equation

HRID 527942 reaction equation
[CH3:1][N:2]([C@@H:10]1[CH2:14][CH2:13][N:12]([C:15]2[C:16]3[CH:23]=[CH:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:17]=3[N:18]=[CH:19][N:20]=2)[CH2:11]1)[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][N:4]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=1.O>CN(C=O)C>[F:46][C:43]1[CH:44]=[CH:45][C:40]([CH2:39][NH:9][C:6]2[CH:7]=[CH:8][C:3]([N:2]([CH3:1])[C@@H:10]3[CH2:14][CH2:13][N:12]([C:15]4[C:16]5[CH:23]=[CH:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:29])[CH3:31])[C:17]=5[N:18]=[CH:19][N:20]=4)[CH2:11]3)=[N:4][CH:5]=2)=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 962WaterHCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 68027541HCID 68027541, compound

Product 1

HCID 68029370HCID 68029370, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (R)—N2-methyl-N2-(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)pyridine-2,5-diamine (0.20 mmol) in DMF (5 mL) were added K2CO3 (0.24 mmol) and 1-Chloromethyl-4-fluoro-benzene (0.24 mmol) at room temperature. The mixture was stirred at 80° C. for 18 hours, poured into water and extracted with EtOAc. The organic layer was washed with water and brine sequentially, then concentrated. The residue was purified by preparative TLC to give the title compound in 30% yield.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine sequentially
  3. concentrationconcentrated
  4. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-e65693a62c30443c9f9b663a0af2084c
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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