7-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl]-5-iodo-7H-pyrrolo[2,3-d]pyrimidine → {7-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}{5-[(diphenylmethylene)amino]pyridin-3-yl}methanone

HRID 82147Notes

Reaction equation

HRID 82147 reaction equation
C([Mg]Cl)(C)C.[Si:6]([O:13][CH2:14][C@@H:15]([N:17]1[C:21]2[N:22]=[CH:23][N:24]=[CH:25][C:20]=2[C:19](I)=[CH:18]1)[CH3:16])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[C:27]1([C:33](=[N:40][C:41]2[CH:42]=[N:43][CH:44]=[C:45]([CH:52]=2)[C:46](N(OC)C)=[O:47])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[Si:6]([O:13][CH2:14][C@@H:15]([N:17]1[C:21]2[N:22]=[CH:23][N:24]=[CH:25][C:20]=2[C:19]([C:46]([C:45]2[CH:44]=[N:43][CH:42]=[C:41]([N:40]=[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:52]=2)=[O:47])=[CH:18]1)[CH3:16])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 708175957-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl]-5-iodo-7H-pyrrolo[2,3-d]pyrimidineHCID 866720805-((Diphenylmethylene)amino)-N-methoxy-N-methylnicotinamideHCID 178418918HCID 178418918, compound

Product 1

HCID 86672079{7-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}{5-[(diphenylmethylene)amino]pyridin-3-yl}methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Isopropyl magnesium chloride (68.8 mL, 138 mmol, 2.0 M in THF) was added to 7-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (52.2 g, 125 mmol) (see Preparation 14) in THF (400 mL) at 0° C., under nitrogen. The mixture was stirred at 0° C. for 1 hour then a solution of 5-[(diphenylmethylene)amino]-N-methoxy-N-methylnicotinamide (47.5 g, 138 mmol) (see Preparation 23) in THF (100 mL) was added dropwise at 0° C. The mixture was warmed to room temperature and stirred at this temperature for 16 hours. The reaction mixture was quenched with 10% aqueous ammonium chloride (250 mL) and extracted with ethyl acetate (2×250 mL).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred at this temperature for 16 hours
  3. customThe reaction mixture was quenched with 10% aqueous ammonium chloride (250 mL)
  4. extractionextracted with ethyl acetate (2×250 mL)

Sources & evidence

ORD record
ord-7f552e74739448478fce6a250438723e
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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