N-Iodosuccinimide → Tert-butyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)methyl)piperidine-1-carboxylate

HRID 1913262Notes

Reaction equation

HRID 1913262 reaction equation
C1C(=O)N([I:8])C(=O)C1.[CH3:9][Si:10]([CH3:48])([CH3:47])[CH2:11][CH2:12][O:13][CH2:14][N:15]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:16]1[N:21]2[N:22]=[CH:23][CH:24]=[C:20]2[N:19]=[C:18]([CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)[CH:17]=1>CC#N>[CH3:46][Si:43]([CH3:44])([CH3:45])[CH2:42][CH2:41][O:40][CH2:39][N:15]([CH2:14][O:13][CH2:12][CH2:11][Si:10]([CH3:9])([CH3:47])[CH3:48])[C:16]1[N:21]2[N:22]=[CH:23][C:24]([I:8])=[C:20]2[N:19]=[C:18]([CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)[CH:17]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 66733904Tert-butyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)piperidine-1-carboxylate

Product 1

HCID 66733306Tert-butyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NIS (288 mg, 1.28 mmoL) was added to a solution of tert-butyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)piperidine-1-carboxylate (Int-12d, 741.6 mg, 1.25 mmoL) in CH3CN (10 mL). The mixture was stirred at room temperature for 1 h. Purification by column chromatography afforded tert-butyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)methyl)piperidine-1-carboxylate (Int-12e): LCMS tR=3.02 Min (5 min run, UV254nm). Mass calculated for, M+717.2, observed m/z 718.3 (M+H).

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-7936ce939a4744dd8fa099fc541ecb14
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

Loading…