Hydrochloric Acid → HCID 13672661, compound

HRID 280474Notes

Reaction equation

HRID 280474 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:11])[N:3]=1.[H-].[Na+].[CH3:14][O:15][C:16](=O)[O:17]C.Cl>O1CCCC1>[CH3:14][O:15][C:16](=[O:17])[NH:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:11])[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 136726584-Cyclopropyl-6-methyl-2-pyrimidinamine

Product 1

HCID 13672661HCID 13672661, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 53.7 g of 2-amino-4-cyclopropyl-6-methylpyrimidine in 1000 ml of tetrahydrofuran is added portionwise, under a nitrogen atmosphere, 42.8 g of 50% sodium hydride while cooling the reaction flask in an ice-water bath. After stirring one hour at 25° C. 58.5 g of dimethylcarbonate is added dropwise at 5° to 25°. The suspension is stirred about 16 hours at ambient temperatures, then 80 ml of concentrated hydrocloride acid is added dropwise under a nitrogen atmosphere while maintaining a reaction temperature of 20° to 25° with external ice-bath cooling. The suspension is stirred 0.5 hour, filtered, and the filtrate is dried over sodium sulfate and concentrated in vacuo to give the subject compound.

Workup

  1. additionis added portionwise, under a nitrogen atmosphere
  2. stirringThe suspension is stirred about 16 hours at ambient temperatures
  3. temperaturewhile maintaining a reaction temperature of 20° to 25° with external ice-bath
  4. temperaturecooling
  5. stirringThe suspension is stirred 0.5 hour
  6. filtrationfiltered
  7. dry with materialthe filtrate is dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give the subject compound

Sources & evidence

ORD record
ord-d073baed0f034b71acc35e8b541f2155
Source dataset
uspto-grants-1986_05
Patent number
US04589909

Reaction notes

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