Diisopropylethylamine → (S)-tert-butyl 2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboxylate

HRID 1892117Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(N(CC)C(C)C)(C)C.Cl[C:25]1[C:26]2[C:33]([CH3:34])=[CH:32][NH:31][C:27]=2[N:28]=[CH:29][N:30]=1>C(O)(C)C>[CH3:1][C@H:2]1[CH2:7][N:6]([C:25]2[C:26]3[C:33]([CH3:34])=[CH:32][NH:31][C:27]=3[N:28]=[CH:29][N:30]=2)[CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9]

Participants

Conditions

Temperature: 120 °C

Procedure

(S)-tert-butyl 2-methylpiperazine-1-carboxylate (3 g, 15 mmol), N,N-diisopropylethylamine (3 ml), and 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (2 g, 12 mmol) were added to isopropanol (10 ml). The solution was heated at 120° C. in a sealed pressure tube for 12 hours. The reaction was concentrated under vacuum, and the residue was purified by flash chromatography (80 g SiO2, 0-5% MeOH: CH2Cl2, 50 min) to give clean (S)-tert-butyl 2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboxylate (1.5 g, 4.5 mmol, 38%).

Workup

concentrationThe reaction was concentrated under vacuum
customthe residue was purified by flash chromatography (80 g SiO2, 0-5% MeOH: CH2Cl2, 50 min)

Sources & evidence

ORD record: ord-e023729ae0a94ee487aee8de536b3c1f
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507672B2

Reaction notes

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