Methyl iodide → 4,6-Dichloro-N-methylpyrimidin-5-amine

HRID 1685179Notes

Reaction equation

HRID 1685179 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].[H-].[Na+].[CH3:12]I>C1COCC1>[Cl:9][C:3]1[C:2]([NH:1][CH3:12])=[C:7]([Cl:8])[N:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 2502744,6-Dichloro-N-methylpyrimidin-5-amineYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Add 5-amino-4,6-dichloropyrimidine (2 g; 0.012 mol) to THF (60 mL). Cool to 0° C. and add portion-wise NaH (0.53 g; 0.013 mol). Stir at 0° C. for 30 min. Add drop-wise methyl iodide (0.7 mL, 0.012 mol). Stir at 0° C. for 1 h and then RT for 30 min. Quench with saturated ammonium chloride aqueous and extract with EA. Evaporate the organic layer and purify the residue through a silica gel column using acetone and hexane as eluent to give the title compound (0.6 g; 27.64%).

Workup

  1. stirringStir at 0° C. for 1 h
  2. waitRT for 30 min
  3. customQuench with saturated ammonium chloride aqueous
  4. extractionextract with EA
  5. customEvaporate the organic layer
  6. custompurify the residue through a silica gel column

Sources & evidence

ORD record
ord-3d2b197eb1a44b4dae3828aee1d0c42b
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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