Dimethylformamide → HCID 44430466, compound

HRID 1984322Notes

Reaction equation

HRID 1984322 reaction equation
[N:1]1([C:8]2[N:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)C=[C:10]([N:17]3[CH2:20][CH:19](OS(C)(=O)=O)[CH2:18]3)[C:9]=2[CH3:26])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C-]#[N:28].[Na+].C[N:31]([CH3:34])C=O>>[N:1]1([C:8]2[N:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:28]=[C:10]([N:17]3[CH2:20][CH:19]([C:34]#[N:31])[CH2:18]3)[C:9]=2[CH3:26])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 86604161HCID 86604161, compound

Product 1

HCID 44430466HCID 44430466, compoundYield 60%

Conditions

Temperature
120 °C

Procedure

A mixture of methanesulfonic acid 1-(6-azepan-1-yl-2-cyclopropyl-5-methyl-pyrimidin-4-yl)-azetidin-3-yl ester 190 (0.3 g, 0.8 mmol) and sodium cyanide (0.047 g, 1.0 mmol) in N,N-dimethylformamide (5 ml) is heated at 120° C. for 24 hours. The mixture is then cooled and concentrated in vacuo. The mixture is diluted with dichloromethane and washed two times with water. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo to afford 0.4 g of a crude mixture, which is purified by column chromatography (dichloromethane/ethanol 98/2). 0.10 g (60%) of 1-(6-azepan-1-yl-2-cyclopropyl-5-methyl-pyrimidin-4-yl]-azetidine-3-carbonitrile 183 is obtained.

Workup

  1. temperatureThe mixture is then cooled
  2. concentrationconcentrated in vacuo
  3. additionThe mixture is diluted with dichloromethane
  4. washwashed two times with water
  5. dry with materialThe combined organic layers are dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford 0.4 g of a crude mixture, which
  8. customis purified by column chromatography (dichloromethane/ethanol 98/2)

Sources & evidence

ORD record
ord-ed9686c3f3b74e45bad4a285ede68212
Source dataset
uspto-grants-2009_06
Patent number
US07544675B2

Reaction notes

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