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

HRID 589955Notes

Reaction equation

[CH:1]1([NH:5][S:6]([N:9]2[C:14]3([CH2:16][CH2:15]3)[CH2:13][N:12]([C:17]3[C:18]4[CH:25]=[CH:24][NH:23][C:19]=4[N:20]=[CH:21][N:22]=3)[CH2:11][CH2:10]2)(=[O:8])=[O:7])[CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[O:32](C(OC(C)(C)C)=O)[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=O.O>CN(C=O)C>[CH:1]1([NH:5][S:6]([N:9]2[C:14]3([CH2:15][CH2:16]3)[CH2:13][N:12]([C:17]3[C:18]4[CH:25]=[CH:24][N:23]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:32])[C:19]=4[N:20]=[CH:21][N:22]=3)[CH2:11][CH2:10]2)(=[O:7])=[O:8])[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

N-cyclobutyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (intermediate 30) (4.4 mmol) was dissolved in dry DMF (15 ml), added K2CO3 (5.28 mmol) and cooled to 0° C. A solution of BOC2O (1.06 g, 4.86 mmol) in dry DMF (5 mL) was added and the reaction mixture was allowed to warm up freely 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 freely 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-18381497fddd43069792b489804e8341
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233964B2

Reaction notes

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