Water → 4-(4-Sulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester

HRID 589944Notes

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([O-])([O-])=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:32]([O:31][C:29]([N:7]1[C:6]2[N:1]=[CH:2][N:3]=[C:4]([N:10]3[CH2:17][C:14]4([CH2:16][CH2:15]4)[N:13]([S:18](=[O:20])(=[O:19])[NH2:21])[CH2:12][CH2:11]3)[C:5]=2[CH:9]=[CH:8]1)=[O:28])([CH3:35])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 0 °C

Procedure

7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid amide (intermediate 1) (1.5 g, 4.86 mmol) was dissolved in dry DMF (20 ml), added Cs2CO3 (1.59 g, 4.86 mmol) and cooled to 0° C. A solution of BOC2O (1.06 g, 4.86 mmol) in dry DMF (10 mL) was added and the reaction mixture was allowed to warm up to rt 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

temperatureto warm up to rt
extractionextracted with EtOAc (3×100 mL)
washThe combined organic phases were washed with H2O (2×50 mL), brine (2×50 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe product was purified by flash chromatography on silica

Sources & evidence

ORD record: ord-c5f289ecaf314a50bdcdd674babef978
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233964B2

Reaction notes

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