Tributylstannane → N-((S)-2,3-dihydro-1H-inden-1-yl)-7-((4aS,6R,7aS)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 222149Notes

Reaction equation

HRID 222149 reaction equation
C(=S)(OC1C=CC=CC=1)O[C@@H:3]1[C@@H:7]2[O:8][CH:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][CH2:11][C@@H:6]2[CH2:5][C@H:4]1[N:20]1[C:24]2[N:25]=[CH:26][N:27]=[C:28]([NH:29][C@@H:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:32][CH2:31]3)[C:23]=2[CH:22]=[CH:21]1.C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[C@@H:30]1([NH:29][C:28]2[C:23]3[CH:22]=[CH:21][N:20]([C@H:4]4[CH2:3][C@@H:7]5[O:8][CH:9]([C:12]6[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=6)[O:10][CH2:11][C@@H:6]5[CH2:5]4)[C:24]=3[N:25]=[CH:26][N:27]=2)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86614244O-[(4aS,6R,7S,7aR)-6-{4-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo-[2,3-d]pyrimidin-7-yl}-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-yl] O-phenyl thiocarbonate

Product 1

HCID 66618654N-((S)-2,3-dihydro-1H-inden-1-yl)-7-((4aS,6R,7aS)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

O-[(4aS,6R,7S,7aR)-6-{4-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo-[2,3-d]pyrimidin-7-yl}-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-yl] O-phenyl thiocarbonate (5.00 g, 7.88 mmol) was dissolved in toluene (150. mL) under an atmosphere of nitrogen and tri-n-butyltin hydride (4.24 mL, 15.8 mmol) was added followed by 2,2′-azo-bis-isobutyronitrile (259 mg, 1.58 mmol). The solution was heated to reflux for 30 min, the mixture was cooled down, the solvent was concentrated to 30 mL and the residue was purified via silica gel chromatography eluting with a gradient of 30 to 100% EtOAc in hexanes to afford the title compound (3.00 g, 79%). LC/MS: Rt=2.12 min, ES+ 483 (AA standard).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 30 min
  3. temperaturethe mixture was cooled down
  4. concentrationthe solvent was concentrated to 30 mL
  5. customthe residue was purified via silica gel chromatography
  6. washeluting with a gradient of 30 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-3bc8248277444a6691de41966f0a41b8
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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