Ethanol → HCID 18460835, compound

HRID 2303304Notes

Reaction equation

HRID 2303304 reaction equation
O.[NH2:2]N.O=C1C2C(=CC=CC=2)C(=O)N1CCN[C:18]1[N:23]=[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=2)[C:21]([C:32]([NH2:34])=[O:33])=[CH:20][N:19]=1.[CH2:35]([OH:37])[CH3:36]>>[NH2:2][CH2:36][CH2:35][O:37][C:18]1[N:23]=[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=2)[C:21]([C:32]([NH2:34])=[O:33])=[CH:20][N:19]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 18460851HCID 18460851, compound

Product 1

HCID 18460835HCID 18460835, compound

Procedure

A 0.2 ml portion of hydrazine monohydrate was added to a mixture of 350 mg of 2-[2-(1,3-dioxo-2,3-dihydroisoindol-2-yl)ethyl]amino-4-(3-methylanilino)pyrimidine-5-carboxamide with 10 ml of ethanol, followed by heating under reflux for 4 hours. The reaction mixture was concentrated under a reduced pressure. A chloroform-methanol mixed solution was added to the thus obtained residue, followed by washing with water, 1 M sodium hydroxide aqueous solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under a reduced pressure, and the resulting residue was recrystallized from ethanol to obtain 140 mg of 2-(2-aminoethoxy)-4-(3-methylanilino)pyrimidine-5-carboxamide (colorless crystals).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under a reduced pressure
  4. additionA chloroform-methanol mixed solution was added to the thus obtained residue
  5. washby washing with water, 1 M sodium hydroxide aqueous solution and saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customthe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-1222f0ada95b49659202a11d5e5681ea
Source dataset
uspto-grants-2002_08
Patent number
US06432963B1

Reaction notes

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