1-Butanol → HCID 86762630, compound

HRID 2409083Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.[CH2:17]([NH:19][CH:20]([C:22]1[N:23]=[CH:24][C:25]2[N:30]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:29]=[CH:28][C:26]=2[N:27]=1)[CH3:21])[CH3:18].CCN(C(C)C)C(C)C.CCCCO>CCOC(C)=O>[CH:14]1([C:12]2[NH:11][N:10]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([N:19]([CH2:17][CH3:18])[CH:20]([C:22]4[N:23]=[CH:24][C:25]5[N:30]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:29]=[CH:28][C:26]=5[N:27]=4)[CH3:21])[N:7]=3)[CH:13]=2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 115 °C

Procedure

A vial was charged with 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-pyrimidin-4-amine (60 mg, 0.25 mmol), N-ethyl-1-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethanamine (367.0 mg, 1.14 mmol), DIPEA (1.3 mL) and n-BuOH (3.5 mL), sealed and heated at 115° C. for 96 h. The reaction mixture was poured into EtOAc, and the organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by SiO2chromatography to afford 103.9 mg (52.35%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-ethyl-N2-(1-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethyl)pyrimidine-2,4-diamine as a racemic mixture. MS (ESI) m/z: 520.3 [M+1]+.

Workup

customsealed
washthe organic layer was washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by SiO2chromatography

Sources & evidence

ORD record: ord-e81a9d161bce49aeb224799a84a2a031
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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