Hydrochloric Acid → 3-[4-(3-Chloro-4-methoxybenzyl-amino)benzothieno[2,3-d]pyrimidin-2-yl]propionic acid

HRID 2298874Notes

Reaction equation

HRID 2298874 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[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19][C:9]=2[N:10]=[C:11]([CH2:13][CH2:14][C:15]([O:17]C)=[O:16])[N:12]=1.[OH-].[Na+].Cl>COCCO>[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[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19][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 10983074Methyl 3-[4-(3-chloro-4-methoxybenzylamino)-benzothieno[2,3-d]pyrimidin-2-yl]propionate

Product 1

HCID 99104203-[4-(3-Chloro-4-methoxybenzyl-amino)benzothieno[2,3-d]pyrimidin-2-yl]propionic acid

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

Methyl 3-[4-(3-chloro-4-methoxybenzylamino)-benzothieno[2,3-d]pyrimidin-2-yl]propionate is dissolved in ethylene glycol monomethyl ether and; after addition of 32% strength NaOH, stirred at 110° for 5 hours. 20% strength HCl is added, and the mixture is then extracted with dichloromethane. Addition of petroleum ether affords 3-[4-(3-chloro-4-methoxybenzylamino)benzothieno[2,3-d]pyrimidin-2-yl]propionic acid, m.p. 218°.

Workup

  1. extractionthe mixture is then extracted with dichloromethane
  2. additionAddition of petroleum ether

Sources & evidence

ORD record
ord-09eea41f05c54019885f6687961d1d68
Source dataset
uspto-grants-2002_12
Patent number
US06495557B1

Reaction notes

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