Hydrochloric Acid → 2-((Thiophen-2-ylmethylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one

HRID 713396Notes

Reaction equation

HRID 713396 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([CH2:8][N:9]([CH2:17][C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)C(=O)OC(C)(C)C)=[N:5][C:4]2[CH2:23][CH2:24][O:25][CH2:26][C:3]1=2.Cl>CO>[S:19]1[CH:20]=[CH:21][CH:22]=[C:18]1[CH2:17][NH:9][CH2:8][C:6]1[NH:7][C:2](=[O:1])[C:3]2[CH2:26][O:25][CH2:24][CH2:23][C:4]=2[N:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136612912tert-butyl (4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl(thiophen-2-ylmethyl)carbamate

Product 1

HCID 1362193232-((Thiophen-2-ylmethylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-oneYield 111.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl(thiophen-2-ylmethyl)carbamate (0.87 g, 2.3 mmol) in methanol (5 mL) was added hydrochloride acid (2.3 mL, 4M in dioxane). The mixture was stirred at ambient temperature for 24 h, filtered and washed with ether to give the title compound as a white solid (710 mg, 98% yield).

Workup

  1. filtrationfiltered
  2. washwashed with ether

Sources & evidence

ORD record
ord-ec13fd9a9c1c4b4599286b3d7632e4ab
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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