Hydrochloric Acid → 2-Chloro-4-methoxy-6-methylpyrimidine

HRID 2413079Notes

Reaction equation

HRID 2413079 reaction equation
N[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH3:10])[N:3]=1.N([O-])=O.[Na+].[OH-].[Na+].[ClH:17]>O>[Cl:17][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH3:10])[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5872364-Methoxy-6-methylpyrimidin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 124905712-Chloro-4-methoxy-6-methylpyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 25.4 g of 2-amino-4-methyl-6-methoxypyrimidine in 150 ml concentrated hydrochloric acid was cooled to ca. 0° C. and treated with a solution of 25.3 g of sodium nitrite in 50 ml water, added over a period of 30-40 minutes. The thick orange reaction mixture was stirred at room temperature for 4-5 hours and then adjusted to pH 10 by addition of 12.5N sodium hydroxide solution. The precipitate was filtered and extracted thoroughly with approximately 600 ml of hot ether. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give 7.2 g of 2-chloro-4-methyl-6-methoxypyrimidine as a white, crystalline solid, m.p. 36°-38° C.

Workup

  1. additionadded over a period of 30-40 minutes
  2. filtrationThe precipitate was filtered
  3. extractionextracted thoroughly with approximately 600 ml of hot ether
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe2e339b38da4681bf209418fe4f70c8
Source dataset
uspto-grants-1985_01
Patent number
US04496392

Reaction notes

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