Neopentylamine → HCID 21941888, compound

HRID 271548Notes

Reaction equation

HRID 271548 reaction equation
[CH2:1]([NH2:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br:7][C:8]1[C:9](Cl)=[N:10][C:11]([Cl:14])=[N:12][CH:13]=1>CO>[Br:7][C:8]1[C:9]([NH:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])=[N:10][C:11]([Cl:14])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 21941888HCID 21941888, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Neopentylamine (30 ml, 0.255 mol) is added dropwise at 0° C. over 20 min to a soln. of 5-bromo-2,4-dichloropyrimidine (29.17 g, 0.128 mol) in MeOH (230 ml). After stirring for 20 min at 0° C., the mixture is warmed to room temperature, stirred for 3 h, and evaporated. The residue is suspended in 300 ml of EtOAc, washed with sat. aq. NaHCO3 soln. (80 ml) and brine (80 ml), dried (MgSO4), and evaporated. The residue is chromagraphed on silica gel column (800 g of silica gel; hexane/EtOAc 5:1) to give the product (A) (32.64 g, 92%). White crystals. 1H-NMR (400 MHz, CDCl3) δ 1.00 (s), 3.36 (d, J=8.0), 5.52-5.61 (br. s), 8.12 (s). Rf 0.48 (hexane/EtOAc 5:1).

Workup

  1. temperaturethe mixture is warmed to room temperature
  2. stirringstirred for 3 h
  3. customevaporated
  4. washwashed with sat. aq. NaHCO3 soln
  5. dry with material(80 ml) and brine (80 ml), dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-056b7a774d5b4606b0a4175c3ae5fac8
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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