1,1,1-Trimethoxybutane → 4-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

HRID 1363592Notes

Reaction equation

HRID 1363592 reaction equation
CO[C:3](OC)(OC)[CH2:4][CH2:5][CH3:6].[NH2:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:21]=1[NH:22][CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[N:19][CH:18]=[CH:17][CH:16]=2>C1(C)C=CC=CC=1.Cl.N1C=CC=CC=1>[CH2:4]([C:3]1[N:22]([CH2:23][C:24]2([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:21]2[C:20]3[N:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=1)[CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 669191884-[(3-Amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol

Product 1

HCID 575154594-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-olYield 69.2%

Reagents, catalysts & solvents 2

HCID 10176127Pyridinium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Trimethylorthobutyrate (1.9 mL, 12.0 mmol) and pyridine hydrochloride (23 mg, 0.2 mmol) were added to a suspension of 4-[(3-amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol (10.0 mmol) in toluene (50 mL). The reaction mixture was heated at reflux overnight and then concentrated under reduced pressure. The residue was triturated with acetonitrile and the resulting solid was isolated by filtration to provide 2.26 g of 4-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-ol as a tan solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with acetonitrile
  5. customthe resulting solid was isolated by filtration

Sources & evidence

ORD record
ord-c8fa798f809546f6a7b12674a69280f1
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Reaction notes

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