Oxalic Acid → (+/-)-1-[3-[[(3,4-Dihydro-2h-1-benzopyran-2-yl)-methyl]amino]propyl]tetrahydro-2(1h)-pyrimidinethione ethanedioate

HRID 352425Notes

Reaction equation

HRID 352425 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH:11]=O.[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][NH:19][C:18]1=[S:23].[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>CO.[Pd]>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH2:11][NH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][NH:19][C:18]1=[S:23]

Participants

6

Reactant 3

HCID 971Oxalic Acid2×HCID 20627851HCID 20627851, compoundHCID 225732481-(3-aminopropyl)tetrahydro-2(1H)-pyrimidinethione

Product 1

HCID 22573245(+/-)-1-[3-[[(3,4-Dihydro-2h-1-benzopyran-2-yl)-methyl]amino]propyl]tetrahydro-2(1h)-pyrimidinethione ethanedioateYield 7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde (0.015 mol) and 1-(3-aminopropyl) tetrahydro-2(1H)-pyrimidinethione (0.01 mol) in methanol (150 ml) was hydrogenated for 2 days at room temperature (atmospheric pressure) with palladium on activated carbon (2 g) as a catalyst. After uptake of H2 (1 eq.), the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 95/5). The pure fractions were collected and the solvent was evaporated. The residue (0.3 g) was dissolved in ethanol (30 ml) and converted into the ethanedioic acid salt (1:1) with ethanedioic acid (0.3 g; 0.0124 mol). The precipitate was filtered off and dried (vacuum), yielding 0.3 g (7%) of (±)-1-[3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)-methyl]amino]propyl]tetrahydro-2(1H)-pyrimidinethione ethanedioate(1:1); mp. 217.6° C. (comp. 14).

Workup

  1. filtrationAfter uptake of H2 (1 eq.), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 95/5)
  4. customThe pure fractions were collected
  5. customthe solvent was evaporated
  6. dissolutionThe residue (0.3 g) was dissolved in ethanol (30 ml)
  7. filtrationThe precipitate was filtered off
  8. customdried (vacuum)

Sources & evidence

ORD record
ord-3f1e38eb69b2463781f694791c0a3e4d
Source dataset
uspto-grants-2004_06
Patent number
US06747045B2

Reaction notes

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