2-Methylpropan-2-olate → N-(4-(Dipropylphosphoryl)phenyl)-2-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 655804Notes

Reaction equation

HRID 655804 reaction equation
CC(C)([O-])C.[CH2:6]([P:9]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)([CH2:11][CH2:12][CH3:13])=[O:10])[CH2:7][CH3:8].Cl[C:22]1[N:30]=[C:29]([I:31])[N:28]=[C:27]2[C:23]=1[N:24]=[CH:25][N:26]2[CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][O:33]1>C1COCC1>[CH2:6]([P:9]([C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:22]2[N:30]=[C:29]([I:31])[N:28]=[C:27]3[C:23]=2[N:24]=[CH:25][N:26]3[CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)=[CH:18][CH:19]=1)([CH2:11][CH2:12][CH3:13])=[O:10])[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 45749132-Methylpropan-2-olateHCID 112107406-Chloro-2-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 599945404-(Dipropylphosphoryl)aniline

Product 1

HCID 86631259N-(4-(Dipropylphosphoryl)phenyl)-2-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Patasium tert-Butoxide (0.19 g, 1.65 mmol) was suspended in 4.5 mL anhydrous THF under nitrogen and cooled to −10° C. in an ice-salt bath. 4-(Dipropylphosphoryl)benzenamine (0.12 g, 0.55 mmol) was added to the suspension and the mixture was stirred at −10° C. for 30 min. 6-Chloro-2-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (Tetrahedron 2002, 58, 7911-7923, 0.18 mg, 0.5 mmol) was then added to the reaction mixture and the content was warmed to room temperature and stirred over night. The reaction mixture was cooled to 0° C., and quenched by the addition of 0.1N HCl (˜500 mL). The mixture was concentrated on a rotavapor. The residue was partitioned between ethyl acetate (10 mL)/water (4 mL), organic layer was separated and washed with 0.1N HCl (4×4 mL), saturated NaHCO3 (4 mL), brine (4 mL), and dried over Na2SO4. The final product was obtained by flash column chromatography on silica gel (7.5% MeOH/DCM).

Workup

  1. temperaturethe content was warmed to room temperature
  2. stirringstirred over night
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customquenched by the addition of 0.1N HCl (˜500 mL)
  5. concentrationThe mixture was concentrated on a rotavapor
  6. customThe residue was partitioned between ethyl acetate (10 mL)/water (4 mL), organic layer
  7. customwas separated
  8. washwashed with 0.1N HCl (4×4 mL), saturated NaHCO3 (4 mL), brine (4 mL)
  9. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-1f5cf1783a2348aea1b0ab0e5235133e
Source dataset
uspto-grants-2011_12
Patent number
US08071609B2

Reaction notes

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