Sodium Sulfate → HCID 178487985, compound

HRID 657113Notes

Reaction equation

HRID 657113 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][C:25]1[C:26]2[CH2:36][CH2:35][C:34](=[O:37])[NH:33][C:27]=2[N:28]=[C:29]([CH:31]=O)[N:30]=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][C:25]1[N:30]=[C:29]([CH2:31][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:28][C:27]2=[N:33][C:34](=[O:37])[CH2:35][CH2:36][C:26]=12

Participants

7

Reactant 5

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68929878HCID 68929878, compoundHCID 866353564-Methyl-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2-carbaldehyde

Product 1

HCID 178487985HCID 178487985, 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 (0.097 g, 0.287 mmol) in 1:1 MeOH/DCM (16 mL) was added 4-methyl-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2-carbaldehyde (0.064 g, 0.287 mmol), NaHCO3 (0.12 g, 1.44 mmol) and excess Na2SO4. The solution was stirred at ambient temperature for 16 h followed by the addition of NaBH(OAc)3 (0.182 g, 0.861 mmol). The resulting solution was stirred for an additional 2 h, then concentrated onto silica gel 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 (0.072 g, 53%).

Workup

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

Sources & evidence

ORD record
ord-c5361223f0734c5f854658c238138177
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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