Phthaloyl chloride → (Tert-butoxy)-n-[2-(1,3-dioxobenzo[c]azolidin-2-yl)pyrimidin-5-yl]carboxamide

HRID 38145

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][N:3]=1.[C:16](Cl)(=[O:26])[C:17]1[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:19](Cl)=[O:20]>N1C=CC=CC=1.CCOC(C)=O>[C:12]([O:11][C:9]([NH:8][C:5]1[CH:6]=[N:7][C:2]([N:1]2[C:19](=[O:20])[C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16]2=[O:26])=[N:3][CH:4]=1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of N-(2-aminopyrimidin-5-yl)(tert-butoxy)carboxamide (0.237 g, 1.0 mmol) in pyridine (1 mL) was added phthaloyl dichloride (0.144 mL, 1.0 mmol). The resulting suspension was stirred at 45° C. for 2 hr, diluted with EtOAc, washed with water and brine, dried and concentrated in vacuo to give crude (tert-butoxy)-N-[2-(1,3-dioxobenzo[c]azolidin-2-yl)pyrimidin-5-yl]carboxamide (0.31 g). ES-MS (M+H)+=341; (M+H-tBu)+=285.

Workup

washwashed with water and brine
customdried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6d84e0d607b74e3cbcd1f84777651352
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524721B2

Linked notes

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