Water → 3-(3-fluoro-4-morpholinophenyl)-6-methyl-2-((pyridin-3-yloxy)methyl)pyrimidin-4(3H)-one

HRID 56270Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C:9]([NH2:11])=O)[CH:2]=1.[F:12][C:13]1[CH:14]=[C:15]([NH:25][C:26](=[O:31])[CH2:27][C:28](=O)[CH3:29])[CH:16]=[CH:17][C:18]=1[N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.CCOC(C)=O.O>C1(C)C(C)=CC=CC=1.C([O-])(C)C.C([O-])(C)C.C([O-])(C)C.C([O-])(C)C.[Ti+4]>[F:12][C:13]1[CH:14]=[C:15]([N:25]2[C:26](=[O:31])[CH:27]=[C:28]([CH3:29])[N:11]=[C:9]2[CH2:8][O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:16]=[CH:17][C:18]=1[N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 165 °C

Procedure

A mixture of 2-(pyridin-3-yloxy)acetamide (120 mg, 0.79 mmol), N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide (221.1 mg, 0.79 mmol) and titanium tetraisopropanolate (1.79 g, 6.30 mmol) in xylene (16 mL) was stirred at 165° C. for 50 h. The mixture was then cooled to rt and 30 mL of EtOAc and 5 mL of water were added. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc) to give the title compound as a yellow solid (0.90 g, 29%). The compound was characterized by the following spectroscopic data:

Workup

temperatureThe mixture was then cooled to rt
filtrationThe resulting mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by a silica gel column chromatography (EtOAc)

Sources & evidence

ORD record: ord-70ab06d206f84891836f8a281c174605
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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