Hydrochloric Acid → 3-[7-(3-chloro-4-methoxybenzylamino)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl]propionic acid

HRID 1836161Notes

Reaction equation

HRID 1836161 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:8]2[N:21]([CH3:22])[N:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:9]=2[N:10]=[C:11]([CH2:13][CH2:14][C:15]([O:17]C)=[O:16])[N:12]=1.[OH-].[Na+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:8]2[N:21]([CH3:22])[N:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:9]=2[N:10]=[C:11]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11774810methyl 3-[7-(3-chloro-4-methoxybenzylamino)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl]propionate

Product 1

HCID 113046363-[7-(3-chloro-4-methoxybenzylamino)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl]propionic acidYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.3 g of methyl 3-[7-(3-chloro-4-methoxybenzylamino)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-propionate are dissolved in 30 ml of tetrahydrofuran (THF) and, after addition of 10 ml of 10% NaOH, stirred at 60° for 8 hours. After addition of 10% HCl, the deposited crystals are separated off and recrystallized from methanol. 3.7 g of 3-[7-(3-chloro-4-methoxybenzylamino)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl]propionic acid, m.p. 178°, are obtained.

Workup

  1. customthe deposited crystals are separated off
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-aa60aaaf815741529cb88e463c8f0110
Source dataset
uspto-grants-2004_08
Patent number
US06777419B1

Reaction notes

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