Water → HCID 44450361, compound

HRID 1984249Notes

Reaction equation

HRID 1984249 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[C-]#N.[Na+].[N:25]12CCN(CC1)C[CH2:26]2.O>CS(C)=O>[CH3:19][C:18]([CH3:21])([CH3:20])[CH2:17][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=1)[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:26]#[N:25])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 9237DabcoHCID 57714136HCID 57714136, compound

Product 1

HCID 44450361HCID 44450361, compoundYield 861.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

(2-Chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-(4-iodo-benzyl)-amine (10.0 g, 24.0 mmoles) and sodium cyanide (5.6 g, 0.12 moles) are dissolved in 40 ml of DMSO and 1,4-diaza bicyclo[2,2,2]octane (0.27 g, 2.4 mmoles) is added at rt. The mixture is stirred at 75° C. for 21 h. Water is added and the organic layer is extracted with AcOEt, washed with brine, dried over magnesum sulfate and concentrated. The crude product is purified by silica gel column chromatography to give 8.4 g of desired 4-[(2,2-dimethyl-propyl)-(4-iodo-benzyl)-amino]-pyrimidine-2-carbonitrile in 86% yield.

Workup

  1. extractionthe organic layer is extracted with AcOEt
  2. washwashed with brine
  3. dry with materialdried over magnesum sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f397259237f24decadaad0ad7ae24780
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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