Water → HCID 71611704, compound

HRID 2409082Notes

Reaction equation

[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([N:16]([CH3:35])[CH2:17][C:18]4[CH:23]=[N:22][CH:21]=[C:20]5[N:24](COCC[Si](C)(C)C)[CH:25]=[CH:26][C:19]=45)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.[NH4+].[OH-]>O1CCCC1>[NH:24]1[C:20]2=[CH:21][N:22]=[CH:23][C:18]([CH2:17][N:16]([CH3:35])[C:12]3[N:11]=[C:10]([NH:9][C:6]4[CH:5]=[C:4]([CH:1]5[CH2:2][CH2:3]5)[NH:8][N:7]=4)[CH:15]=[CH:14][N:13]=3)=[C:19]2[CH:26]=[CH:25]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methyl-N2-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methyl)pyrimidine-2,4-diamine (108 mg, 0.22 mmol) and tetrabutyl ammonium fluoride (580 mg, 2.2 mmol) in tetrahydrofuran (20 mL) was heated at 80° C. for 18 h. The reaction mixture was poured into water (100 mL) and the pH was adjusted to ca. 10 by adding an NH4OH solution. The mixture was extracted with EtOAc (50 mL×3) and the combined extracts dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC to afford 18 mg (22.7%) of N2-((1H-pyrrolo[2,3-c]pyridin-4-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methylpyrimidine-2,4-diamine as a white solid. 1H NMR (500 MHZ, MeOD-d4) δ 8.62 (s, 1H), 7.82 (d, 2H), 7.59 (d, 1H), 6.59 (d, 1H), 6.12 (d, 1H), 5.84 (brs, 1H), 5.13 (s, 2H), 3.03 (s, 3H), 1.58 (brs, 1H), 0.68 (d, 2H), 0.27 (d, 2H); MS (ESI): m/z=361.2 [M+1]+.

Workup

extractionThe mixture was extracted with EtOAc (50 mL×3)
dry with materialthe combined extracts dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-18a4e91a4fa7466f95984691553e8410
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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