Methyl Isobutyl Ketone → HCID 178463877, compound

HRID 1679269Notes

Reaction equation

HRID 1679269 reaction equation
O.C(O)(=O)C[C:4]([CH2:9][C:10]([OH:12])=O)([C:6](O)=O)O.S(O)(O)(=O)=O.C([NH:22][C:23](=[NH:27])[NH:24][CH2:25][CH3:26])C.OS(O)(=O)=O.O=S(=O)=O.[CH2:37](C(C)=O)[CH:38](C)C>O.N>[OH:12][C:10]1[CH:9]=[C:4]([CH3:6])[N:22]=[C:23]([N:24]([CH2:25][CH3:26])[CH2:37][CH3:38])[N:27]=1

Participants

7

Reactant 4

HCID 7909Methyl Isobutyl Ketone2×HCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 24681Fuming sulfuric acidHCID 178464618HCID 178464618, compound

Product 1

HCID 178463877HCID 178463877, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

A mixture of citric acid monohydrate (126.0 g) and diethylguanidine sulphate (82.0 g) was added to 15% oleum (250 ml), keeping the temperature below 30° C by external cooling. After stirring at the ambient temperature for 15 minutes to complete solubilisation the solution was heated at 70° C for 80 minutes, cooled by external cooling to 0° C, and carefully diluted with water (350 ml) and with ammonia solution (s.g. 0.880, 600 ml). The resulting slurry was heated to reflux, methyl isobutyl ketone (10 ml) being added to prevent excessive frothing. Refluxing was continued for 16 hours, after which the mixture was cooled to 70°-80° C and methyl isobutyl ketone (600 ml) added to dissolve the precipitate. The ketonic phase was separated, washed with water (2 × 100 ml) whilst still hot, and then cooled and dried over anhydrous magnesium sulphate. Evaporation of the solvent yielded chromatographically pure 4-hydroxy-2-diethylamino-6-methylpyrimidine, melting point 133°- 135° C.

Workup

  1. customthe temperature below 30° C
  2. temperaturewas heated at 70° C for 80 minutes
  3. temperaturecooled
  4. temperatureby external cooling to 0° C
  5. temperatureThe resulting slurry was heated
  6. temperatureto reflux
  7. temperatureRefluxing
  8. waitwas continued for 16 hours
  9. temperatureafter which the mixture was cooled to 70°-80° C
  10. dissolutionto dissolve the precipitate
  11. customThe ketonic phase was separated
  12. washwashed with water (2 × 100 ml) whilst still hot
  13. temperaturecooled
  14. dry with materialdried over anhydrous magnesium sulphate
  15. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b01c2b8ab80e48719af0309771fcf2a3
Source dataset
uspto-grants-1978_03
Patent number
US04080326

Reaction notes

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