Water → HCID 44450349, compound

HRID 1984253Notes

Reaction equation

HRID 1984253 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH:21]=[N:20][CH:19]=[N:18]3)=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[C-]#N.[Na+].[N:30]12CCN(CC1)C[CH2:31]2.O>CS(C)=O>[CH3:24][C:23]([CH3:26])([CH3:25])[CH2:22][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)=[CH:12][CH:11]=1)[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:31]#[N:30])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 9237DabcoHCID 57714113HCID 57714113, compound

Product 1

HCID 44450349HCID 44450349, compoundYield 69,167.102%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

(2-Chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-(4-[1,2,4]triazol-1-ylmethyl-benzyl)-amine (160 mg, 0.43 mmoles) and sodium cyanide (0.1 g, 2.2 mmoles) are dissolved in 5 ml of DMSO and 1,4-diaza bicyclo[2,2,2]octane (23 mg, 0.2 mmoles) is added at rt. The mixture is stirred at rt for 5 h at 70° C. 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 50 g of desired 4-[(2,2-dimethyl-propyl)-(4-[1,2,4]triazol-1-ylmethyl-benzyl)-amino]-pyrimidine-2-carbonitrile in 32% 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-bf90d253eeed43d581a65ad996002c90
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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