Triethylamine → HCID 66898703, compound

HRID 1892120Notes

Reaction equation

Cl[C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:12]12[N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:16]([CH2:17][CH2:18]1)[CH2:15][NH:14][CH2:13]2.C(N(CC)CC)C>C(O)(C)C>[CH3:11][C:10]1[C:3]2[C:2]([N:14]3[CH2:13][CH:12]4[N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:16]([CH2:17][CH2:18]4)[CH2:15]3)=[N:7][CH:6]=[N:5][C:4]=2[NH:8][CH:9]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (25 mg, 0.15 mmol) and tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate (30 mg, 0.14 mmol) in isopropanol (2 ml) was added triethylamine (36 μL, 0.26 mmol). The reaction was heated at 180° C. for 30 min in the microwave, then concentrated under vacuum. The residue was purified by prep HPLC (Sunfire C18 30×50 mm, 10-90% H2O/MeOH w/0.01% TFA, 15 min, 35 ml/min, 220 nm) to give tert-butyl 3-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (35 mg, 0.10 mmol, 66%).

Workup

concentrationconcentrated under vacuum
customThe residue was purified by prep HPLC (Sunfire C18 30×50 mm, 10-90% H2O/MeOH w/0.01% TFA, 15 min, 35 ml/min, 220 nm)

Sources & evidence

ORD record: ord-b199ed2d24bc48878a539810b0f0700c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507672B2

Reaction notes

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