Dichloromethane → 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047151Notes

Reaction equation

HRID 2047151 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=[CH:26][CH:27]=[C:4]2[N:3]=1.[I:28]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(Cl)Cl>CC#N.[Cl-].[Na+].O.O>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:14])[CH3:15])[N:5]2[N:25]=[CH:26][C:27]([I:28])=[C:4]2[N:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 772312195-chloro-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 772312185-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amineYield 101.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To crude 5-chloro-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (7.9 g) in CH3CN (100 mL) was added N-iodosuccinimide (4.3 g, 19.2 mmol) and the resulting mixture was stirred at room temperature for 30 mins, at which time LC/MS confirmed full conversion of starting material to product. Saturated sodium thiosulfate solution (˜20 mL) was added and stirring continued for 5 minutes before the mixture was transferred to a separatory funnel using CH2Cl2 (30 mL) and H2O (30 mL). Brine (50 mL) was added and organics were extracted with CH2Cl2 (4×40 mL), dried (Na2SO4) and concentrated in vacuo to give crude 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine as a light brown liquid (10.4 g). LCMS: 2.95 mins, m/z=555.1 (MH+).

Workup

  1. stirringstirring
  2. waitcontinued for 5 minutes before the mixture
  3. customwas transferred to a separatory funnel
  4. extractionorganics were extracted with CH2Cl2 (4×40 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-445118441df0400d8d6c5ec58c3bd89e
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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