Sodium Sulfate → HCID 178486367, compound

HRID 657115Notes

Reaction equation

HRID 657115 reaction equation
[ClH:1].[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[C:16](=[O:17])[CH:15]=[N:14][C:13]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[N:21][C:12]2=3)[CH2:5][CH2:4]1.[CH3:24][O:25][C:26]1[C:27]2[CH2:37][CH2:36][C:35](=[O:38])[NH:34][C:28]=2[N:29]=[C:30]([CH:32]=O)[N:31]=1.C([O-])(O)=O.[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(Cl)Cl>[ClH:1].[CH3:24][O:25][C:26]1[N:31]=[C:30]([CH2:32][NH:2][CH:3]2[CH2:4][CH2:5][N:6]([CH2:9][CH2:10][N:11]3[C:16](=[O:17])[CH:15]=[N:14][C:13]4[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[N:21][C:12]3=4)[CH2:7][CH2:8]2)[NH:29][C:28]2=[N:34][C:35](=[O:38])[CH2:36][CH2:37][C:27]=12

Participants

7

Reactant 5

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68929878HCID 68929878, compoundHCID 866353574-(Methyloxy)-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2-carbaldehyde

Product 1

HCID 178486367HCID 178486367, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 4-[2-(4-amino-1-piperidinyl)ethyl]-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one hydrochloride (0.105 g, 0.309 mmol) in 1:1 MeOH/DCM (16 mL) was added 4-(methyloxy)-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2-carbaldehyde (0.074 g, 0.309 mmol), NaHCO3 (0.13 g, 1.55 mmol), and excess Na2SO4. The solution was stirred at ambient temperature for 16 h followed by the addition of NaBH(OAc)3 (0.196 g, 0.927 mmol). The resulting solution was stirred for an additional 2 h, then concentrated onto silica gel under vacuum and the crude residue was purified by column chromatography (silica gel) using a DCM/DCM-MeOH—NH4OH (90:10:1) gradient to yield the free base of the desired product as a yellowish oily film (0.114 g, 75%).

Workup

  1. stirringThe resulting solution was stirred for an additional 2 h
  2. concentrationconcentrated onto silica gel under vacuum
  3. customthe crude residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-032f5926dfe74554b97f29c48d1edad8
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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