Pyridine → 6-(morpholin-4-yl)-2-[2-oxo-2-(2',3',5',6'-tetrahydrospiro[indole-3,4'-pyran]-1(2H)-yl)ethyl]pyrimidin-4(3H)-one

HRID 2278630Notes

Reaction equation

HRID 2278630 reaction equation
N1C=CC=CC=1.[O:7]1[CH2:12][CH2:11][C:10]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH2:13]2)[CH2:9][CH2:8]1.Cl.CN(C)CCCN=C=NCC.[N:33]1([C:39]2[N:40]=[C:41]([CH2:46][C:47]([O-])=[O:48])[NH:42][C:43](=[O:45])[CH:44]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.[Na+]>CN(C)C=O>[N:33]1([C:39]2[N:40]=[C:41]([CH2:46][C:47](=[O:48])[N:14]3[C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:10]4([CH2:11][CH2:12][O:7][CH2:8][CH2:9]4)[CH2:13]3)[NH:42][C:43](=[O:45])[CH:44]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 589750752',3',5',6'-Tetrahydrospiro[indoline-3,4'-pyran]HCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 1360696186-(morpholin-4-yl)-2-[2-oxo-2-(2',3',5',6'-tetrahydrospiro[indole-3,4'-pyran]-1(2H)-yl)ethyl]pyrimidin-4(3H)-oneYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.8 ml of pyridine, 378 mg of 1,2,2′,3′,5′,6′-hexahydrospiro[3H-indole-3,4′-[4H]pyran] and 575 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 679 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (example 1d, step 2d) in 11.3 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 16 hours, and then concentrated under reduced pressure. The residue is taken up in 25 ml of water and 20 ml of ethyl acetate, and then left to stir at ambient temperature for 1 hour. The precipitate formed is filtered off, and then rinsed successively with water and diethyl ether. 640 mg of 6-(morpholin-4-yl)-2-[2-oxo-2-(2′,3′,5′,6′-tetrahydrospiro[indole-3,4′-pyran]-1(2H)-yl)ethyl]pyrimidin-4(3H)-one are thus obtained in the form of an off-white powder, the characteristics of which are the following:

Workup

  1. concentrationconcentrated under reduced pressure
  2. wait20 ml of ethyl acetate, and then left
  3. stirringto stir at ambient temperature for 1 hour
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washrinsed successively with water and diethyl ether

Sources & evidence

ORD record
ord-a3e40332f7604859b0f72e65e47512e7
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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