(+-)-2-Butanol → N-(2-(2-bromophenoxy)pyrimidin-5-yl)-4-phenylphthalazin-1-amine

HRID 593996Notes

Reaction equation

[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][C:5]1[N:10]=[CH:9][C:8]([NH2:11])=[CH:7][N:6]=1.Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:19][N:18]=1.CC(O)CC.C1C2C(=CC=CC=2)C=NN=1>CCCCCC>[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]([NH:11][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:19][N:18]=2)=[CH:9][N:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

2-(2-Bromophenoxy)pyrimidin-5-amine (3.01 g, 11.3 mmol), 1-chloro-4-phenylphthalazine (2.72 g, 11.3 mmol), and butan-2-ol (56.6 ml, 11.3 mmol) were placed in a sealed tube. The reaction vessel was sealed and mixture heated to 120° C. After 1.5 h, LCMS showed mainly product as [M+H]+=470 and a small amount of bromo starting material. 200 mg of phthalazine was added. After another 3.5 h, the reaction was cooled to RT. Hexane was added to allow a yellow solids to precipitate. The yellow solids were filtered and recrystallized with DCM and hexanes. The resulting dark brown solids were dried under vacuum overnight, affording the product, N-(2-(2-bromophenoxy)pyrimidin-5-yl)-4-phenylphthalazin-1-amine.

Workup

customThe reaction vessel was sealed
waitAfter another 3.5 h
temperaturethe reaction was cooled to RT
customto precipitate
filtrationThe yellow solids were filtered
customrecrystallized with DCM and hexanes
customThe resulting dark brown solids were dried under vacuum overnight

Sources & evidence

ORD record: ord-7be43db68edc41f1a00b1e773e49fb35
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242961B2

Reaction notes

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