Hydrochloric Acid → 4-[4-(3,4-Methylenedioxybenzylamino)-6-methyl-thieno-[2,3-d-]pyrimidin-2-yl]-benzoic acid

HRID 366374Notes

Reaction equation

HRID 366374 reaction equation
[CH2:1]1[O:31][C:30]2[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]3[C:9]4[CH:26]=[C:25]([CH3:27])[S:24][C:10]=4[N:11]=[C:12]([C:14]4[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=4)[N:13]=3)=[CH:4][C:3]=2[O:2]1.[OH-].[Na+].Cl>O1CCCC1>[CH2:1]1[O:31][C:30]2[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]3[C:9]4[CH:26]=[C:25]([CH3:27])[S:24][C:10]=4[N:11]=[C:12]([C:14]4[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:22][CH:23]=4)[N:13]=3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 98029154-[4-(3,4-Methylenedioxybenzylamino)-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl]-benzoic acid methylester

Product 1

HCID 98883244-[4-(3,4-Methylenedioxybenzylamino)-6-methyl-thieno-[2,3-d-]pyrimidin-2-yl]-benzoic acidYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.1 g of methyl 4-[4-(3,4-methylenedioxybenzylamino)-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl]-benzoate, 30 ml of 2N NaOH and 30 ml of tetrahydrofuran is heated at 100° for 6 hours. After cooling and acidification of the solution with 20% HCl, the mixture is further worked up in the customary manner. 0.75 g of 4-[4-(3,4-methylenedioxybenzylamino)-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl]-benzoic acid is obtained, m.p. >250°.

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-099980c9907e46318237a255103072a7
Source dataset
uspto-grants-2000_10
Patent number
US06130223

Reaction notes

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