1,4-Dioxane → ethyl 4-(3-(2-(aminomethyl)acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882141Notes

Reaction equation

HRID 882141 reaction equation
C(OC([NH:8][CH2:9][C:10](=[CH2:34])[C:11]([NH:13][C:14]1[CH:15]=[C:16]([C:20]2[C:21]3[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][NH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:17]=[CH:18][CH:19]=1)=[O:12])=O)(C)(C)C.O1CCOCC1>Cl>[NH2:8][CH2:9][C:10](=[CH2:34])[C:11]([NH:13][C:14]1[CH:15]=[C:16]([C:20]2[C:21]3[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][NH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:17]=[CH:18][CH:19]=1)=[O:12]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 89630003ethyl 4-(3-(2-((tert-butoxycarbonylamino)methyl) acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Product 1

HCID 89630004ethyl 4-(3-(2-(aminomethyl)acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 4-(3-(2-((tert-butoxycarbonylamino)methyl) acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (50 mg, 0.11 mmol) in 4 M HCl in dioxane solution (537 μL, 2.15 mmol) was stirred for 1 hour. The reaction mixture was quenched with aqueous saturated sodium bicarbonate (500 μL) and extracted with ethyl acetate (×3). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with 0-20% MeOH/DCM to give ethyl 4-(3-(2-(aminomethyl)acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C19H20N5O3 [M+H]+: 366, found 366.

Workup

  1. customThe reaction mixture was quenched with aqueous saturated sodium bicarbonate (500 μL)
  2. extractionextracted with ethyl acetate (×3)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 0-20% MeOH/DCM

Sources & evidence

ORD record
ord-5e19673c2688472bae15413192bdf2d1
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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