1,3-Diiodo-5,5-dimethylimidazolidine-2,4-dione → tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl]ethyl]carbamate

HRID 1775300Notes

Reaction equation

HRID 1775300 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[N:8]([CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:6]=2[N:7]=1.[I:28]N1C(C)(C)C(=O)N(I)C1=O.C([O-])(O)=O.[Na+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([I:28])=[C:9]([CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[N:8]([CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 2005341,3-Diiodo-5,5-dimethylimidazolidine-2,4-dioneHCID 516892Sodium BicarbonateHCID 87428127Tert-butyl 2-(2-chloro-6-(diethoxymethyl)-7h-pyrrolo[2,3-d]pyrimidin-7-yl)ethylcarbamate

Product 1

HCID 89825123tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl]ethyl]carbamateYield 22.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.1 g (0.00025 mole) of tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]ethyl]carbamate in acetonitrile (2 mL) was added 1,3-Diiodo-5,5-dimethylhydantoin (95 mg, 1 eq), and solid NaHCO3 (63 mg, 3 eq). Stir at room temperature for 16 hrs. Filter, concentrate and then column with hexane/ethylacetate (0-50%) to afford tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl]ethyl]carbamate as a pale yellow solid 0.03 g. LCMS (ESI) 525 (M+H).

Workup

  1. filtrationFilter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-c18c1dddf20b412989a57a3f953abd9f
Source dataset
uspto-grants-2016_02
Patent number
US09260442B2

Reaction notes

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