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

HRID 2278490Notes

Reaction equation

HRID 2278490 reaction equation
[F:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([CH2:9][C:10]([O-:12])=O)=[N:4][C:3]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[Na+].[CH3:20][CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[F:30])[NH:22]1>>[F:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([CH2:9][C:10]([N:22]2[C:23]3[C:28](=[C:27]([F:30])[CH:26]=[CH:25][CH:24]=3)[CH2:29][CH:21]2[CH3:20])=[O:12])=[N:4][C:3]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 573882254-fluoro-2-methyl-2,3-dihydro-1H-indoleHCID 136069585Sodium (5-fluoro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 1363786645-fluoro-2-[2-((+)-2-methyl-4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-oneYield 60.1%

Procedure

The product is prepared by following the procedure described in example 1a (step 5a) using 125 mg of sodium (5-fluoro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate obtained in step 2a of example 6a and 74 mg of (+)-2-methyl-4-fluoro-2,3-dihydro-1H-indole (reference example 5a). After silica column purification: eluent 98/02 dichloromethane/methanol, 105 mg of 5-fluoro-2-[2-((−)-2-methyl-4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one are obtained in the form of a solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter silica column purification

Sources & evidence

ORD record
ord-0ed20da5c58c428c9fa4fbf4132c6673
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

Loading…