Ammonia → tert-butyl 3-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)azetidine-1-carboxylate

HRID 516167Notes

Reaction equation

HRID 516167 reaction equation
O1CCCC1.[NH3:6].Cl[C:8]1[C:9]2[C:16]([I:17])=[CH:15][N:14]([CH:18]3[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19]3)[C:10]=2[N:11]=[CH:12][N:13]=1.C(Cl)(Cl)Cl>O>[NH2:6][C:8]1[C:9]2[C:16]([I:17])=[CH:15][N:14]([CH:18]3[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19]3)[C:10]=2[N:11]=[CH:12][N:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6212ChloroformHCID 8028TetrahydrofuranHCID 89871028tert-butyl 3-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)azetidine-1-carboxylate

Product 1

HCID 89870888tert-butyl 3-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Tetrahydrofuran (2.5 ml) and 28% aqueous ammonia (2.5 ml) were added to the tert-butyl 3-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)azetidine-1-carboxylate (350 mg) obtained in Step 1 above. The reaction mixture was stirred at 100° C. for 1.5 hours using a microwave reactor. Chloroform and water were added thereto to separate the organic layer. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound as a white solid (340 mg). Physical properties: m/z [M+H]+ 416.0

Workup

  1. customto separate the organic layer
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ae7c3d10dd264ce6aa3dcf1793734cac
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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