Water → HCID 136138825, compound

HRID 2278515Notes

Reaction equation

HRID 2278515 reaction equation
Cl.CN(C)CCCN=C=NCC.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[CH2:22][OH:23].[F:24][C:25]1[C:30](=[O:31])[NH:29][C:28]([CH2:32][C:33]([O-])=[O:34])=[N:27][C:26]=1[N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.[Na+].O>CN(C=O)C.N1C=CC=CC=1.ClCCl>[F:24][C:25]1[C:30](=[O:31])[NH:29][C:28]([CH2:32][C:33]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH:14]2[CH2:22][OH:23])=[O:34])=[N:27][C:26]=1[N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

8

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27946642,3-dihydro-1H-indol-2-ylmethanolHCID 136069585Sodium (5-fluoro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136138825HCID 136138825, compoundYield 28.2%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

198 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 105 mg of (−)-(2,3-dihydro-1H-indol-2-yl)methanol (reference example 8a) are added to a solution of 207 mg of sodium (5-fluoro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate in 6 ml of DMF and 6 ml of pyridine. The reaction medium is stirred at ambient temperature for 18 hours and then a mixture of water and dichloromethane is added. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is purified on a silica column, eluent: 95/05 dichloromethane/methanol, so as to give 77 mg of 5-fluoro-2-[2-((+)-2-hydroxymethyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one, the characteristics of which are the following:

Workup

  1. additionis added
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis purified on a silica column, eluent

Sources & evidence

ORD record
ord-16883278a28a4f2f9dcab14f58c6e928
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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