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

HRID 713388Notes

Reaction equation

HRID 713388 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[NH2:8][CH2:9][C:10]1[NH:11][C:12](=[O:20])[C:13]2[CH2:19][O:18][CH2:17][CH2:16][C:14]=2[N:15]=1.C([BH3-])#N.C(O)(=O)C>C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:8][CH2:9][C:10]1[NH:11][C:12](=[O:20])[C:13]2[CH2:19][O:18][CH2:17][CH2:16][C:14]=2[N:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 73642-ThiophenecarboxaldehydeHCID 498716Cyano-borohydrideHCID 1357418942-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-one

Product 1

HCID 1362193232-((Thiophen-2-ylmethylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-oneYield 49.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of thiophene-2-carbaldehyde (0.021 mL, 0.22 mmol), 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (40 mg, 0.22 mmol), and siliabond cyanoborohydride (240 mg, 0.24 mmol, 1 mmol/g) in ethanol (1 mL) was stirred at ambient temperature for 10 minutes. Acetic acid (0.013 mL, 0.22 mmol) was then added, and the mixture was stirred at ambient temperature for another 5 minutes. The reaction mixture was concentrated in vacuo and purified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0, methanol: dichloromethane, 1:99 to 10:90) to provide the title compound (30 mg, 49% yield). m/z 278.1 (M+1), retention time=0.89 min.

Workup

  1. stirringthe mixture was stirred at ambient temperature for another 5 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0, methanol: dichloromethane, 1:99 to 10:90)

Sources & evidence

ORD record
ord-41d9c84289f045cc8515943e788530bb
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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