Water → HCID 136196460, compound

HRID 2278645Notes

Reaction equation

HRID 2278645 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

673 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 378 mg of (−)-(2,3-dihydro-1H-indol-2-yl)methanol (reference example 13d) are added to a solution of 640 mg of sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate in 20 ml of DMF and 20 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: gradient: dichloromethane/methanol from 100/0 to 95/05, so as to give 456 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-795c9e66dd394379a57e3400a1f48b40
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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