Morpholine → 8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200636Notes

Reaction equation

HRID 2200636 reaction equation
C([N:4]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH2:16][OH:17])[C:9](=[O:18])[N:8]([CH2:19][CH3:20])[C:7]=2[N:6]=[C:5]1[Cl:21])C=C.N1CCOCC1>C1COCC1.CS(C)=O.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>[Cl:21][C:5]1[NH:4][C:12]2[C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH2:16][OH:17])[C:9](=[O:18])[N:8]([CH2:19][CH3:20])[C:7]=2[N:6]=1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 904025367-allyl-8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 904034598-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dioneYield 66.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-allyl-8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (3.8 g, 12.18 mmol) in THF (40 mL) and DMSO (10 mL) was added tetrakis(triphenylphosphine)palladium(0) (800 mg, 0.693 mmol) and morpholine (5.4 mL, 62.07 mmol). The reaction was degassed and refilled with nitrogen 3 times. The reaction was stirred at room temperature overnight. The mixture was poured into water (20 mL) and ethyl acetate (100 mL). The solid precipitate was collected, washed with ethyl acetate, and dried under vacuum to give 8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (2.2 g, 66.4% yield) as grey solid. LCMS retention time 0.404 min; LCMS MH+ 273.

Workup

  1. customThe reaction was degassed
  2. additionrefilled with nitrogen 3 times
  3. additionThe mixture was poured into water (20 mL) and ethyl acetate (100 mL)
  4. customThe solid precipitate was collected
  5. washwashed with ethyl acetate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-9ed9f71d9eb34074be1885f46a494eb5
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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