Sulfuric Acid → HCID 178433455, compound

HRID 572635Notes

Reaction equation

HRID 572635 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:12]=[C:11](Cl)[N:10]=[C:9]([CH3:14])[N:8]=1>[OH-].[Na+]>[Cl:6][C:7]1[N:8]=[C:9]([CH3:14])[N:10]=[C:11]([OH:2])[CH:12]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 2349974,6-Dichloro-2-methylpyrimidine

Product 1

HCID 178433455HCID 178433455, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To stirred solution of 13M sulfuric acid (125 mL) at about 0° C., 4,6-dichloro-2-methylpyrimidine (20.0 g, 307 mmol) was added portion wise over about 30 min. The solution was then stirred at about 0° C. for about 1.5 h and the reaction was allowed to warm to ambient temperature over about 1.5 h. The reaction was allowed to stir at RT overnight. The acidic mixture was poured into stirred 6N sodium hydroxide (500 mL) in ice, maintaining the temperature <10° C. and stirred for about 10 min. The white solid was collected and washed with warm water to afford 6-chloro-2-methylpyrimidin-4-ol 40.2 g (91%) 1H NMR (400 MHz, DMSO) δ: 12.85 (brs, 1H), 6.34 (s, 1H), 2.30 (s, 3H). LC/MS (Table 1, Method d) Rt=0.74 min; MS m/z: 145.1 (M+H).

Workup

  1. temperatureto warm to ambient temperature over about 1.5 h
  2. stirringto stir at RT overnight
  3. additionThe acidic mixture was poured
  4. temperaturemaintaining the temperature <10° C.
  5. stirringstirred for about 10 min
  6. customThe white solid was collected
  7. washwashed with warm water

Sources & evidence

ORD record
ord-44aa0efe17e34299ac32bafe5e5651c4
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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