Sodium Hydroxide → HCID 86726639, compound

HRID 1506237Notes

Reaction equation

HRID 1506237 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:13]3[C:14]4[CH:20]=[CH:19][N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:15]=4[N:16]=[CH:17][C:12]=3[C:11](=[O:29])[NH:10][C:9]2=[O:30])[CH2:4][CH2:3]1.[C:31]([C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)#[N:32].B.N1C=CC=CC=1C.[OH-].[Na+]>CO.C(O)(=O)C>[O:30]=[C:9]1[N:8]([CH:5]2[CH2:4][CH2:3][N:2]([CH2:37][C:36]3[CH:39]=[CH:40][C:33]([C:31]#[N:32])=[CH:34][CH:35]=3)[CH2:7][CH2:6]2)[C:13]2[C:14]3[CH:20]=[CH:19][N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[C:15]=3[N:16]=[CH:17][C:12]=2[C:11](=[O:29])[NH:10]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 660424-CyanobenzaldehydeHCID 16217944Borane;2-methylpyridineHCID 86726638HCID 86726638, compound

Product 1

HCID 86726639HCID 86726639, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

1-(Piperidin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[3′,2′:5,6]pyrido[4,3-d]pyrimidine-2,4(3H,7H)-dione hydrochloride (50 mg, 0.111 mmol) and 4-cyanobenzaldehyde (29 mg, 0.22 mmol) in a mixture of methanol (2 ml) and acetic acid (0.2 mL) were stirred with 2-picoline borane (50 mg, 0.47 mmol) at room temperature for 2 days. After addition of 1 M aqueous sodium hydroxide, the reaction mixture was extracted with a mixture of ethyl acetate and 2-propanol, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v)) to give the title compound as a colorless solid (23.4 mg, yield 40%).

Workup

  1. extractionthe reaction mixture was extracted with a mixture of ethyl acetate and 2-propanol
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v))

Sources & evidence

ORD record
ord-7c4bf4ede0ae43f59c12a9490a939df3
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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