Hydrochloric Acid → 2-chloro-6-methylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 1910452Notes

Reaction equation

HRID 1910452 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][C:9]([CH3:11])=[CH:8][C:6]=2[N:7]=1.[OH-:13].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[NH:3][C:4](=[O:13])[C:5]2[S:10][C:9]([CH3:11])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 127242682,4-Dichloro-6-methylthieno[3,2-d]pyrimidine

Product 1

HCID 1363597872-chloro-6-methylthieno[3,2-d]pyrimidin-4(3H)-oneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4-dichloro-6-methylthieno[3,2-d]pyrimidine (450 mg, 2.05 mmol), aqueous NaOH (1N, 4 mL) and THF (4 mL) was stirred at room temperature under N2. The reaction was monitored by HPLC until the reaction was completed. Then the mixture was neutralized to PH 5 by addition of 2N aqueous HCl. The solid was filtrated and dried to give 380 mg of 2-chloro-6-methylthieno[3,2-d]pyrimidin-4(3H)-one (yield was 92%) as a yellow solid. MS obsd. (ESI+) [(M+H)+]: 201.

Workup

  1. filtrationThe solid was filtrated
  2. customdried

Sources & evidence

ORD record
ord-f1444c152b824f1bae8381be8ed4024a
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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