Water → Tert-butyl 4-[8-(tert-butoxycarbonylsulfamoyl)-5,8-diazaspiro[2.5]octan-5-yl]pyrrolo[2,3-d]pyrimidine-7-carboxylate

HRID 589959Notes

Reaction equation

HRID 589959 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:17][C:14]3([CH2:16][CH2:15]3)[N:13]([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:12][CH2:11]2)=[N:3][CH:2]=1.[C:22]([O-:25])([O-:24])=O.[Cs+].[Cs+].[O:28](C(OC(C)(C)C)=O)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=O.O>CN(C=O)C>[C:5]([O:24][C:22]([NH:21][S:18]([N:13]1[C:14]2([CH2:16][CH2:15]2)[CH2:17][N:10]([C:4]2[C:5]3[CH:9]=[CH:8][N:7]([C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:28])[C:6]=3[N:1]=[CH:2][N:3]=2)[CH2:11][CH2:12]1)(=[O:20])=[O:19])=[O:25])([CH3:9])([CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 90495Di-tert-butyl dicarbonateHCID 574100947-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid amide2×

Product 1

HCID 68295965Tert-butyl 4-[8-(tert-butoxycarbonylsulfamoyl)-5,8-diazaspiro[2.5]octan-5-yl]pyrrolo[2,3-d]pyrimidine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid amide (intermediate 1) (1.95 mmol) was dissolved in dry DMF (15 ml), added Cs2CO3 (4.29 mmol), BOC2O (4.29 mmol) and stirred at rt for 16 h. The crude mixture was treated with water (150 mL) and extracted with EtOAc (3×100 mL). The combined organic phases were washed with H2O (2×50 mL), brine (2×50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica using EtOAc in heptane as eluent.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe combined organic phases were washed with H2O (2×50 mL), brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-684782151efb44a2b30e4f105d6c5583
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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