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

HRID 1854965Notes

Reaction equation

HRID 1854965 reaction equation
Cl[C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([C@@H:12]3[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:25]>CC(O)C>[NH2:25][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([C@@H:12]3[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86714512(R)-tert-butyl 3-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate

Product 1

HCID 71014221(R)-tert-butyl 3-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (R)-tert-butyl 3-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate (2.0 g, 4.32 mmol) in IPA saturated with NH3 (20 mL) was stirred at 100° C. for 12 h in a 100 mL of autoclave. The organic layer was concentrated and purified on silica gel chromatography (eluted with PE:EtOAc=1:1) to afford (R)-tert-butyl 3-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate (1.5 g, 78% in yield).

Workup

  1. concentrationThe organic layer was concentrated
  2. custompurified on silica gel chromatography (eluted with PE:EtOAc=1:1)

Sources & evidence

ORD record
ord-bfd6978b394d4c078f8c54a15ab4ec2b
Source dataset
uspto-grants-2015_02
Patent number
US08962831B2

Reaction notes

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