Water → HCID 136196460, compound

HRID 2278648Notes

Reaction equation

HRID 2278648 reaction equation
Cl.[CH3:2]N(C)CCCN=C=NCC.[N:13]1([C:19]2[N:24]=[C:23]([CH2:25][C:26](=[O:42])[N:27]3[C:35]4[C:30](=[C:31](C5C=NC=CC=5)[CH:32]=[CH:33][CH:34]=4)[CH2:29][CH2:28]3)[NH:22][C:21](=[O:43])[CH:20]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.N1(C2N=C(CC([O-])=O)NC(=O)C=2)CCOCC1.[Na+].[OH2:62]>CN(C=O)C.N1C=CC=CC=1.ClCCl>[OH:62][CH2:2][CH:28]1[CH2:29][C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:27]1[C:26](=[O:42])[CH2:25][C:23]1[NH:22][C:21](=[O:43])[CH:20]=[C:19]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[N:24]=1

Participants

8

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetateHCID 136069611HCID 136069611, compound

Product 1

HCID 136196460HCID 136196460, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

890 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 500 mg of (+)-(2,3-dihydro-1H-indol-2-yl)methanol (reference example 13d) are added to a solution of 876 mg of sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate in 26 ml of DMF and 26 ml of pyridine. The reaction medium is stirred at ambient temperature for 18 hours 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: gradient: dichloromethane/methanol from 100/0 to 95/05, so as to give 708 mg of 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-33ddb505c0014eab877e2530f2db5fb5
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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