Morpholine → HCID 59299569, compound

HRID 2386602Notes

Reaction equation

HRID 2386602 reaction equation
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[NH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27].N1CCOCC1>CN(C=O)C.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:27][CH2:26][CH2:25][CH:24]=[CH2:23])[C:4]=2[N:3]=1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 10340Sodium CarbonateHCID 707041-Pentene, 5-bromo-HCID 592995327-Allyl-8-chloro-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 59299569HCID 59299569, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.10 g, 0.44 mmol) was dissolved in DMF (1.5 ml) containing sodium carbonate (0.12 g, 0.49 mmol) and 5-bromopentene (0.07 g, 0.49 mmol) and the mixture stirred for 18 h. On completion of alkylation, morpholine (0.5 ml) and tetrakis(triphenylphosphine) palladium (0) (0.08 g, 0.07 mmol) were added and stirring continued for 3.5 h. The reaction was diluted with ethyl acetate (10 ml) washed sequentially with 2N hydrochloric acid (2×5 ml) and brine (3×5 ml) and the organic isolated, dried (MgSO4) and concentrated. The crude product was suspended in methanol (2 ml) and purified on an aminopropyl SPE (5 g) eluting with methanol first then 5% acetic acid in methanol to elute the title compound which was isolated as a white solid after concentration (0.039 g, 35%). NMR; (400 MHz, d6-DMSO) 1.75 (m, 2H), 2.05 (m, 2H), 3.85 (t, 2H, J=7 Hz), 4.95 (m, 1H), 5.05 (m, 1H), 5.8 (m, 1H), 11.1 (br s, 1H), one exchangeable proton not observed to δH 13; m/z 255 [MH+]

Workup

  1. stirringstirring
  2. waitcontinued for 3.5 h
  3. washwashed sequentially with 2N hydrochloric acid (2×5 ml) and brine (3×5 ml)
  4. dry with materialthe organic isolated, dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified on an aminopropyl SPE (5 g)
  7. washeluting with methanol first
  8. wash5% acetic acid in methanol to elute the title compound which
  9. customwas isolated as a white solid
  10. concentrationafter concentration (0.039 g, 35%)

Sources & evidence

ORD record
ord-8a68bc45dcb94705a0a17ecf6e13f863
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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