Diisopropylethylamine → HCID 86272864, compound

HRID 1505598Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:14]=2)[C:11](=[O:25])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[F:26])[N:4]=1.Cl[C:28]1[C:29]2[CH:36]=[CH:35][NH:34][C:30]=2[N:31]=[CH:32][N:33]=1.C(N(C(C)C)CC)(C)C>CC(O)(C)C>[N:31]1[C:30]2[NH:34][CH:35]=[CH:36][C:29]=2[C:28]([NH:1][CH2:2][C:3]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]([F:22])([F:23])[F:24])[CH:14]=3)[C:11](=[O:25])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[F:26])[N:4]=2)=[N:33][CH:32]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Under nitrogen, to 2-(aminomethyl)-5-fluoro-3-(3-(2,2,2-trifluoroethoxy)phenyl)quinazolin-4(3H)-one (73 mg, 0.20 mmol, 1.0 equiv) in t-BuOH (0.2 mL) at 23° C. was added 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (34 mg, 0.22 mmol, 1.1 equiv) and diisopropylethylamine (70 μL, 0.40 mmol, 2.0 equiv). After stirring for 36 hr at 120° C. in a sealed tube, the reaction mixture was concentrated in vacuo and the residue was purified by preparative TLC eluting with CH2Cl2/MeOH to afford 20 mg of the title compound (21% yield).

Workup

concentrationthe reaction mixture was concentrated in vacuo
customthe residue was purified by preparative TLC
washeluting with CH2Cl2/MeOH

Sources & evidence

ORD record: ord-e9f592720d3046f9bea4007f28c77e4e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216985B2

Reaction notes

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