Hydrochloric Acid → n-(4-(5-Methylaminomethyl-1-(2,6-difluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxo-3-(4-methoxyphenyl)thieno[2,3-d]pyrimidin-6-yl)phenyl)-n'-methoxyureahydrochloride

HRID 1027955Notes

Reaction equation

HRID 1027955 reaction equation
[CH2:1]([N:8]([CH2:10][C:11]1[C:19]2[C:18](=[O:20])[N:17]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[C:16](=[O:29])[N:15]([CH2:30][C:31]3[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=3[F:38])[C:14]=2[S:13][C:12]=1[C:39]1[CH:44]=[CH:43][C:42]([NH:45][C:46]([NH:48][O:49][CH3:50])=[O:47])=[CH:41][CH:40]=1)C)C1C=CC=CC=1.[ClH:51]>C(O)C.[C].[Pd]>[ClH:51].[CH3:1][NH:8][CH2:10][C:11]1[C:19]2[C:18](=[O:20])[N:17]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[C:16](=[O:29])[N:15]([CH2:30][C:31]3[C:32]([F:38])=[CH:33][CH:34]=[CH:35][C:36]=3[F:37])[C:14]=2[S:13][C:12]=1[C:39]1[CH:40]=[CH:41][C:42]([NH:45][C:46]([NH:48][O:49][CH3:50])=[O:47])=[CH:43][CH:44]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86620014HCID 86620014, compound

Product 1

HCID 87155673n-(4-(5-Methylaminomethyl-1-(2,6-difluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxo-3-(4-methoxyphenyl)thieno[2,3-d]pyrimidin-6-yl)phenyl)-n'-methoxyureahydrochlorideYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixed solution of N-(4-(5-((benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-3-(4-methoxyphenyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-N′-methoxyurea (2.0 g, 2.87 mmol) synthesized in Reference Example 19, 10%-palladium-carbon (200 mg), 1N hydrochloric acid (3 ml) in ethanol (40 ml) was stirred under hydrogen atmosphere at room temperature for 72 hours. The reaction mixture was subjected to filtration and the filtrate was concentrated to dryness to give the title compound (1.77 g, 96%) as white powders.

Workup

  1. filtrationThe reaction mixture was subjected to filtration
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-eb0b4abd89084c26bdf3969ce8002efb
Source dataset
uspto-grants-2014_05
Patent number
US08735401B2

Reaction notes

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