Dimethylformamide → HCID 66744048, compound

HRID 2364008Notes

Reaction equation

HRID 2364008 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:15][C:14]3[C:13](=[O:16])[NH:12][C:11]4([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[NH:10][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.CN(C=O)C.[C:27](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:28].[Na+]>C(=O)C>[CH2:27]([N:19]1[CH2:20][CH2:21][C:11]2([NH:10][C:9]3[CH:8]=[C:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[S:15][C:14]=3[C:13](=[O:16])[NH:12]2)[CH2:17][CH2:18]1)[CH3:28]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 5049666Sodium triacetoxyborohydrideHCID 66742948HCID 66742948, compound

Product 1

HCID 66744048HCID 66744048, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 177AcetaldehydeSolvent

Procedure

A mixture of 6′-(pyridin-4-yl)-1′H-spiro[piperidine-4,2′-thieno[3,2-d]pyrimidin]-4′(3′H)-one in DMF (0.16 M, 0.50 mL, 0.080 mmol), acetaldehyde in DMF (0.20 M, 1 mL, 0.20 mmol) and sodium triacetoxyborohydride (40 mg, 0.19 mmol) was stirred for 16 h at room temperature. The reaction mixture was extracted with EtOAc (3.5 mL) and 2% aqueous sodium hydrogen carbonate (1 mL). After evaporating the organic solvent, the crude product was chromatographed on preparative HPLC (YMC CombiPrep. Hydrosphere C18, 10 mM NH4HCO3 in water/MeCN) to afford the title compound (2.4 mg, 9.1%):

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (3.5 mL) and 2% aqueous sodium hydrogen carbonate (1 mL)
  2. customAfter evaporating the organic solvent
  3. customthe crude product was chromatographed on preparative HPLC (YMC CombiPrep. Hydrosphere C18, 10 mM NH4HCO3 in water/MeCN)

Sources & evidence

ORD record
ord-e11701b21f4f482484928f326407040c
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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