5-fluoro-2-[2-(4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one → 5-fluoro-2-[2-(5-fluoro-2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one

HRID 2278485Notes

Reaction equation

HRID 2278485 reaction equation
F[C:2]1[C:7](=[O:8])[NH:6][C:5](CC([O-])=O)=[N:4][C:3]=1N1CCOCC1.[Na+].[F:20][C:21]1[C:22](=[O:46])[NH:23][C:24]([CH2:33][C:34]([N:36]2[C:44]3[C:39](=[C:40]([F:45])[CH:41]=[CH:42][CH:43]=3)[CH2:38][CH2:37]2)=[O:35])=[N:25][C:26]=1[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>>[N:4]1[CH:3]=[CH:2][C:7](=[O:8])[NH:6][CH:5]=1.[F:20][C:21]1[C:22](=[O:46])[NH:23][C:24]([CH2:33][C:34]([N:36]2[C:37]3[C:42](=[CH:41][C:40]([F:45])=[CH:39][CH:38]=3)[CH2:43][CH:44]2[CH3:2])=[O:35])=[N:25][C:26]=1[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 1360695655-fluoro-2-[2-(4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-oneHCID 136069585Sodium (5-fluoro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 2

HCID 206954-HydroxypyrimidineHCID 1363786635-fluoro-2-[2-(5-fluoro-2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-oneYield 66.8%

Procedure

5-Fluoro-2-[2-(5-fluoro-2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl)-3H-pyrimidin-4-one is prepared by following the procedure described in example 1a (step 5a) using 182 mg of sodium (5-fluoro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate (obtained in step 2a) and 197 mg of 5-fluoro-2-methyl-2,3-dihydro-1H-indole (reference example 1a). After silica column purification, eluent: 98/02 dichloromethane/methanol, 85 mg of 5-fluoro-2-[2-(5-fluoro-2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one are obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. customAfter silica column purification, eluent

Sources & evidence

ORD record
ord-e73767702ba8412da970c37cdbf6df69
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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