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

HRID 1285084Notes

Reaction equation

HRID 1285084 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 2amino-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-94dc46d8fb8642d29412913bcd5a3a39
Source dataset
uspto-grants-1986_01
Patent number
US04565567

Reaction notes

Loading…