Water → Tert-butyl 8-(2-chlorofuro[3,2-d]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate

HRID 1038848Notes

Reaction equation

[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[Cl:18][C:19]1[N:20]=[C:21](Cl)[C:22]2[O:27][CH:26]=[CH:25][C:23]=2[N:24]=1.O.CCOC(C)=O>O1CCOCC1>[Cl:18][C:19]1[N:20]=[C:21]([N:8]2[CH2:7][CH2:6][C:5]3([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]3)[CH2:10][CH2:9]2)[C:22]2[O:27][CH:26]=[CH:25][C:23]=2[N:24]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (0.83 g, 3.4 mmol, Alfa Aesar), 2,4-dichlorofuro[3,2-d]pyrimidine (0.65 g, 3.4 mmol, ArkPharm) and TEA (0.96 mL, 6.9 mmol) in 1,4-dioxane (35 mL) was stirred at about 25° C. for about 12 h. Water (4 mL) and EtOAc (25 mL) were added and the layers were separated. The organic layer was concentrated under reduced pressure to give tert-butyl 8-(2-chlorofuro[3,2-d]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate (1.25 g, 55%): LC/MS (Table 2, Method f) Rt=2.12 min; MS m/z: 393 (M+H)+.

Workup

customthe layers were separated
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-f8362b8cd12a4588ab303eac133a9ada
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551981B2

Reaction notes

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