Diisopropylethylamine → 5-chloro-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 1423319Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.C(N([CH2:19][CH3:20])C(C)C)(C)C.[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl.[C:30]([O-:33])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:30][O:33][CH2:19][CH2:20][Si:22]([CH3:28])([CH3:23])[CH3:21])[CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To 5-chloropyrazolo[1,5-a]pyrimidin-7-amine (6.7 g, 39.7 mmol) in CH2Cl2 (30 mL) was added N,N-diisopropylethylamine (48.0 mL, 275.6 mmol) followed by 2-(Trimethylsilyl)ethoxymethyl chloride (25.0 mL, 141.7 mmol). The reaction was heated at 45° C. for 3 hours before being allowed to cool to room temperature. The reaction mixture was then poured into a separatory funnel containing ˜100 mL saturated NaHCO3 solution and CH2Cl2 (50 mL). Organics were then extracted with CH2Cl2 (4×50 mL), dried (Na2SO4) and concentrated in vacuo to give a thick orange liquid. Gradient column chromatography on silica eluting with 5% to 15% EtOAc/hexanes gave crude 5-chloro-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine as a colorless liquid.

Workup

temperatureto cool to room temperature
additionThe reaction mixture was then poured into a separatory funnel
extractionOrganics were then extracted with CH2Cl2 (4×50 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customto give a thick orange liquid

Sources & evidence

ORD record: ord-9add28e6664c4c04bb7dc2d90c77a31b
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927562B2

Reaction notes

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