Hydrochloric Acid → 6-Pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-one

HRID 2374310Notes

Reaction equation

HRID 2374310 reaction equation
C([N:4]1[C:12]2[C:11]3=[N:13][N:14]=[N:15][N:10]3[C:9](=[O:16])[N:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:7]=2[N:6]=[CH:5]1)C=C.N1CCOCC1.N#N.Cl>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[CH2:17]([N:8]1[C:7]2[N:6]=[CH:5][NH:4][C:12]=2[C:11]2=[N:13][N:14]=[N:15][N:10]2[C:9]1=[O:16])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 8083MorpholineHCID 598538529-Allyl-6-pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-one

Product 1

HCID 1359846826-Pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-oneYield 35%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 9-allyl-6-pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-one (0.10 g, 0.35 mmol) and morpholine (0.2 mL, 2.0 mmol) in THF (3 mL) was degassed for 5 min using N2 and tetrakis(triphenylphosphine)palladium(0) (0.10 g, 0.086 mmol) was added to the mixture. After being stirred at room temperature overnight, the reaction mixture was mixed with 2 M HCl aqueous solution and DCM. The organic layer was separated, dried over Na2SO4 and concentrated. The residue was purified using preparative LCMS to provide the product as a white powder (0.030 g, 35%). LCMS calculated for C10H14N7O (M+H): 248.0; found: 248.0.

Workup

  1. customwas degassed for 5 min
  2. additionwas added to the mixture
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-8022b49ac4bf44699bfc823c77390629
Source dataset
uspto-grants-2008_12
Patent number
US07462624B2

Reaction notes

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