Methanol → HCID 18460824, compound

HRID 2303305Notes

Reaction equation

HRID 2303305 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]CC3C=CC=CC=3)[CH:13]=2)[C:8]([C:26]([NH2:28])=[O:27])=[CH:7][N:6]=1.C1COCC1.CO.[H][H]>[C].[Pd].CN(C=O)C>[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[C:8]([C:26]([NH2:28])=[O:27])=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 15458393HCID 15458393, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18460824HCID 18460824, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A 100 mg portion of 10% palladium-carbon powder was added to a mixture of 869 mg of 2-(2-aminoethylamino)-4-(3-benzyloxyanilino)pyrimidine-5-carboxamide with THF, methanol and DMF, followed by stirring at room temperature for 3 days in an atmosphere of hydrogen under ordinary pressure. The reaction mixture was filtered, and the filtrate was concentrated under a reduced pressure. By Ad:. recrystallizing the resulting residue from an ethyl acetate-methanol mixed solvent, 217 mg of 2-(2-aminoethylamino)-4-(3-hydroxyanilino)pyrimidine-5-carboxamide was obtained (light brown solid).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. customrecrystallizing the resulting residue from an ethyl acetate-methanol mixed solvent

Sources & evidence

ORD record
ord-aaf05490efff4c389a01c7fcc6486d04
Source dataset
uspto-grants-2002_08
Patent number
US06432963B1

Reaction notes

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