2-Aminoresorcinol → HCID 136355298, compound

HRID 1890485Notes

Reaction equation

HRID 1890485 reaction equation
Cl.CN(C)CCCN=C=NCC.[NH2:13][C:14]1[C:20]([OH:21])=[CH:19][CH:18]=[CH:17][C:15]=1[OH:16].[N:22]1([C:28]2[NH:29][CH:30]([CH2:35][C:36]([O-])=[O:37])[NH:31][C:32](=[O:34])[CH:33]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[Na+]>N1C=CC=NC=1>[OH:16][C:15]1[CH:17]=[CH:18][CH:19]=[C:20]([OH:21])[C:14]=1[NH:13][C:36](=[O:37])[CH2:35][C:30]1[NH:31][C:32](=[O:34])[CH:33]=[C:28]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:29]=1

Participants

5

Reactant 3

HCID 694512-AminoresorcinolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86762005HCID 86762005, compound

Product 1

HCID 136355298HCID 136355298, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 9260PyrimidineSolvent

Procedure

1.19 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 946 mg of 2-aminoresorcinol are added to a solution of 1 g of sodium [4-(morpholin-4-yl)-6-oxo-dihydropyrimidin-2-yl]acetate in 8 ml of pyrimidine. The reaction mixture is stirred at ambient temperature for 18 hours, and then concentrated under reduced pressure. Water and ethyl acetate are added and the resulting mixture is thus stirred for 30 minutes. The precipitate formed is filtered off, and rinsed with water, ethyl ether and petroleum ether. The solid obtained is dried under vacuum. 904 mg of N-(2,6-dihydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]-acetamide are obtained in the form of a red solid, which is used as it is in the next stage.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater and ethyl acetate are added
  3. stirringthe resulting mixture is thus stirred for 30 minutes
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washrinsed with water, ethyl ether and petroleum ether
  7. customThe solid obtained
  8. customis dried under vacuum

Sources & evidence

ORD record
ord-6ea8f5d956a7430fb2ea82262147e5e1
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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