Ethyl Acetate → HCID 9932550, compound

HRID 1828884Notes

Reaction equation

HRID 1828884 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:5][NH:6][C:7]1[C:8]2[N:17]([CH3:18])[N:16]=[C:15]([CH2:19][CH2:20][CH3:21])[C:9]=2[N:10]=[C:11]([CH2:13]Cl)[N:12]=1.[NH2:27][CH2:28][CH2:29][CH2:30][OH:31].C(OCC)(=O)C>CN(C=O)C.O.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:5][NH:6][C:7]1[C:8]2[N:17]([CH3:18])[N:16]=[C:15]([CH2:19][CH2:20][CH3:21])[C:9]=2[N:10]=[C:11]([CH2:13][NH:27][CH2:28][CH2:29][CH2:30][OH:31])[N:12]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 90863-Amino-1-propanolHCID 11395281HCID 11395281, compound

Product 1

HCID 9932550HCID 9932550, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2 g of 7-(3-chloro-4-methoxybenzylamino)-5-chloromethyl-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine in 10 ml of DMF is treated with 5 ml of 3-aminopropanol and stirred at room temperature for two hours. It is then diluted with water and extracted with ethyl acetate. The oily product obtained after customary work-up is dissolved in alcoholic HCl and treated with ethyl acetate until turbidity. The precipitated crystals are filtered off with suction and recrystallized from isopropanol/ethyl acetate. 3.1 g of 7-(3-chloro-4-methoxybenzylamino)-5-(3-hydroxypropylaminomethyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine are obtained in the form of its dihydrochloride.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe oily product obtained after customary work-up
  3. filtrationThe precipitated crystals are filtered off with suction
  4. customrecrystallized from isopropanol/ethyl acetate

Sources & evidence

ORD record
ord-5a315fd59aea4185985d4e902c767127
Source dataset
uspto-grants-2006_06
Patent number
US07060823B2

Reaction notes

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