Water → HCID 57714127, compound

HRID 1984248Notes

Reaction equation

HRID 1984248 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]([CH3:14])([CH3:13])[CH2:11][NH2:12].C([O-])([O-])=O.[K+].[K+].O>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][CH2:11][C:10]([CH3:14])([CH3:13])[CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 79882Neopentylamine

Product 1

HCID 57714127HCID 57714127, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dichloropyrimidine (25 g, 0.16 moles) and 2,2-dimethyl-propylamine (25 ml, 0.21 moles) are dissolved in 250 ml of THF and K2CO3 (33.1 g, 0.24 mmoles) is added at rt. The mixture is refluxed at rt for 8 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 22 g of desired (2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine in 67% 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-4af0c8b4abbe430e9f4f269b749e2277
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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