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

HRID 617571Notes

Reaction equation

HRID 617571 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[C:13]3[CH:18]=[C:17]([CH3:19])[S:16][C:14]=3[N:15]=2)=[CH:6][CH:5]=1.[OH-].[Na+].Cl>O1CCCC1>[CH2:29]1[O:28][C:25]2[CH:26]=[CH:27][C:22]([CH2:21][NH:20][C:12]3[C:13]4[CH:18]=[C:17]([CH3:19])[S:16][C:14]=4[N:15]=[C:10]([C:7]4[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=4)[N:11]=3)=[CH:23][C:24]=2[O:30]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 4-[4-(3,4-methylenedioxybenzylamino)-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl]-benzoic acid methylester (1.1 g), 2N NaOH (30 ml), and tetrahydrofuran (30 ml) is heated 6hours to 100° C. After cooling and acidifing the solution with 20% HCl, the usual work up yields 4-[4-(3,4-methylenedioxybenzylamino)-6-methyl-thieno-[2,3-d-]pyrimidin-2-yl]-benzoic acid (0.75 g), Mp. >250° C.

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-e8998f2db66648f0a63f6a47ea449fff
Source dataset
uspto-grants-1999_09
Patent number
US05948911

Reaction notes

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