Water → HCID 13424620, compound

HRID 1285197Notes

Reaction equation

HRID 1285197 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.Cl[C:11]([O:13][CH3:14])=[O:12].[OH2:15].[OH-].[Na+].[O:18]1[CH2:22]CC[CH2:19]1>>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:11]([O:13][CH3:14])=[O:12])[N:5]=[C:4]([NH:9][C:19]([O:18][CH3:22])=[O:15])[CH:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6586Methyl chloroformateHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 674322,4-Diamino-6-chloropyrimidine

Product 1

HCID 13424620HCID 13424620, compound

Procedure

A solution of 21.6 g (0.15 mol) of 6-chloro-2,4-diaminopyrimidine in 100 ml of dry tetrahydrofuran is treated with 50 g (0.45 mol) of potassium t-butylate while stirring, whereupon the yellow suspension obtained is cooled to 0° and treated with a solution of 42.5 g (0.45 mol) of methyl chloroformate in 60 ml of dry tetrahydrofuran. The mixture is stirred at 0° for 1 hour and at room temperature overnight, treated with water while cooling with ice, adjusted with 3N sodium hydroxide solution to pH 10 and extracted with ethyl acetate. The organic phase is washed with 3N hydrochloric acid while cooling with ice, dried over magnesium sulphate and evaporated. The residue obtained is chromatographed on silica gel while eluting with toluene/ethyl acetate (7:3), there being obtained pure dimethyl 6-chloro-2,4-pyrimidinedicarbamate.

Workup

  1. customobtained
  2. temperatureis cooled to 0°
  3. stirringThe mixture is stirred at 0° for 1 hour and at room temperature overnight
  4. temperaturewhile cooling with ice
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with 3N hydrochloric acid
  7. temperaturewhile cooling with ice
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe residue obtained
  11. customis chromatographed on silica gel
  12. washwhile eluting with toluene/ethyl acetate (7:3), there

Sources & evidence

ORD record
ord-23932f2cb39a4910812881df6c93549a
Source dataset
uspto-grants-1986_01
Patent number
US04565869

Reaction notes

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