(Dimethyl sulfide)trihydroboron → HCID 22034144, compound

HRID 1634551Notes

Reaction equation

HRID 1634551 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[C:18]3[N:17]=[C:16]([CH3:19])[N:15]=[C:14]([NH:20][CH2:21]CCC(N)=O)[C:13]=3[N:12]([CH3:27])[CH:11]=2)=[C:5]([CH3:28])[CH:4]=1.B.CSC>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:10][CH2:11][NH:12][CH2:13][CH2:21][NH:20][C:14]2[C:13]3[N:12]([CH3:27])[CH:11]=[C:10]([C:6]4[C:5]([CH3:28])=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=4[CH3:9])[C:18]=3[N:17]=[C:16]([CH3:19])[N:15]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 131723743HCID 131723743, compound

Product 1

HCID 22034144HCID 22034144, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-(4-methoxyphenyl)-N-(2-{[7-(4-methoxy-2,6-dimethylphenyl)-2,5-dimethylpyrrolo[2,3-e]pyrimidin-4-yl]aminoethyl)acetamide in anhydrous THF (5 mL) and stir under N2. Add borane-dimethylsulfide complex (0.2 mL, 10.0 M in THF) and heat to reflux for 14 h. Quench by addition of N,N′-dimethyl-1,2-ethylenediamine (0.21 mL) in MeOH (5 mL) and stir for 1 h at ambient temperature. Concentrate under reduced pressure and purify the residue by preparative TLC, eluting with 10% MeOH in CH2Cl2. Dissolve the residue in a minimum amount of MeOH then add HCl in EtOAc (2 mL) and triturate with Et2O to obtain the title compound as a solid (HCl salt)

Workup

  1. temperatureto reflux for 14 h
  2. customQuench by addition of N,N′-dimethyl-1,2-ethylenediamine (0.21 mL) in MeOH (5 mL)
  3. stirringstir for 1 h at ambient temperature
  4. concentrationConcentrate under reduced pressure
  5. custompurify the residue by preparative TLC
  6. washeluting with 10% MeOH in CH2Cl2
  7. dissolutionDissolve the residue in a minimum amount of MeOH
  8. customadd HCl in EtOAc (2 mL) and triturate with Et2O

Sources & evidence

ORD record
ord-8c92eedcffab47f4816454c300b320cd
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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