Ammonium Hydroxide → 1,1-dimethylethyl 4-[2-(4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-1-piperidinecarboxylate

HRID 1910056Notes

Reaction equation

HRID 1910056 reaction equation
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:3]=1.[OH-].[NH4+:28]>>[NH2:28][C:9]1[C:10]2[C:2]([Br:1])=[CH:3][N:4]([CH2:12][CH2:13][CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 866636851,1-dimethylethyl 4-[2-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-1-piperidinecarboxylate

Product 1

HCID 668239481,1-dimethylethyl 4-[2-(4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-1-piperidinecarboxylateYield 101%

Conditions

Temperature
90 °C

Procedure

To 1,1-dimethylethyl 4-[2-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-1-piperidinecarboxylate (320 mg, 0.721 mmol) in a 5 ml sealable vial was added ammonium hydroxide (1.5 mL, 38.5 mmol). The vial was then capped and heated at 90° C. overnight. The reaction was then cooled and the solid was isolated filtration and washed with NH4OH. The solid was then air dried to give 1,1-dimethylethyl 4-[2-(4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-1-piperidinecarboxylate (309 mg) as an off white solid that contained a small amount of starting material. It was used without further purification. LC-MS (ES) m/z=424.4 [M+H]+.

Workup

  1. customThe vial was then capped
  2. temperatureThe reaction was then cooled
  3. customthe solid was isolated
  4. filtrationfiltration
  5. washwashed with NH4OH
  6. customair dried

Sources & evidence

ORD record
ord-32326e2092564ff2a2304aa10d18bc30
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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