Methanol → HCID 86699675, compound

HRID 1487177Notes

Reaction equation

HRID 1487177 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([Cl:23])[C:5]2[C:10]([CH3:12])([CH3:11])[C:9](=O)[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:6]=2[N:7]=1.B#B.CO>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([Cl:23])[C:5]2[C:10]([CH3:12])([CH3:11])[CH2:9][N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6328200Diboron2×HCID 86699676HCID 86699676, compound

Product 1

HCID 86699675HCID 86699675, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro-7-(4-methoxybenzyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (270 mg, 0.77 mol) in tetrahydrofuran (10 mL) was added diborane (1 M in tetrahydrofuran, 3.85 mL, 3.85 mmol) dropwise under nitrogen. The mixture was refluxed overnight. After cooling, methanol (2 mL) was added dropwise to decompose the excessive diborane. The solvent was removed and the residue was purified by silica gel column chromatography to afford the product

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureAfter cooling
  3. customThe solvent was removed
  4. customthe residue was purified by silica gel column chromatography
  5. customto afford the product

Sources & evidence

ORD record
ord-818b85e563334d9c91936950b8765e7d
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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