Diisopropylethylamine → 4-(trans-2,5-dimethylpiperazin-1-yl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 1892126Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][NH:3]1.C(N(CC)C(C)C)(C)C.Cl[C:19]1[C:20]2[C:27]([CH3:28])=[CH:26][NH:25][C:21]=2[N:22]=[CH:23][N:24]=1>C(O)(C)C>[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:19]1[C:20]2[C:27]([CH3:28])=[CH:26][NH:25][C:21]=2[N:22]=[CH:23][N:24]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Trans-2,5-dimethylpiperazine (1 g, 8.8 mmol), N,N-diisopropylethylamine (1 ml) and 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (2 g, 11.9 mmol) were added to isopropanol (10 ml). The solution was heated in a microwave at 150° C. for 6 hours, then concentrated under vacuum. The material was purified by prep HPLC (Sunfire C18 30×250 mm column. 10-100% MeCN:H2O (10 mM NH4OAc), 18 min., 45 ml/min.) to give 4-(trans-2,5-dimethylpiperazin-1-yl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (0.30 g, 14%).

Workup

concentrationconcentrated under vacuum
customThe material was purified by prep HPLC (Sunfire C18 30×250 mm column. 10-100% MeCN:H2O (10 mM NH4OAc), 18 min., 45 ml/min.)

Sources & evidence

ORD record: ord-67fc71f8a09e42ac855d99cb421ddf50
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507672B2

Reaction notes

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