Morpholine-4-carboximidamide Hydrobromide → HCID 178418872, compound

HRID 8606Notes

Reaction equation

HRID 8606 reaction equation
CO[C:3](=[O:18])[CH:4]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[C:5]([O:7]C)=O.C[O-].[Na+].Br.[N:23]1([C:29]([NH2:31])=[NH:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CO>[CH3:17][O:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[O:9][C:4]1[C:3]([OH:18])=[N:30][C:29]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:31][C:5]=1[OH:7]

Participants

5

Reactant 3

HCID 2806564Morpholine-4-carboximidamide HydrobromideHCID 10942334Sodium MethoxideHCID 21803851Dimethyl-(3-methoxyphenoxy)malonate

Product 1

HCID 178418872HCID 178418872, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of dimethyl-(3-methoxyphenoxy)-malonate (11.19 g) in methanol (100 ml) was added sodium methylate (6.48 g). The yellow solution was stirred for 6 h at rt. Then, morpholine-4-carboxamidine hydrobromide (8.40 g) was added and the mixture was stirred at rt for 16 h. The solvent was removed in vacuo and the residue was dissolved in water (150 ml) and extracted twice with diethyl ether (150 ml). The aqueous phase was acidified with 10% aq. citric acid. The solid that separated was collected, washed with water, evaporated twice from EA, and dried under high vacuum to give 5-(3-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidine-4,6-diol (9.66 g) as a beige powder. LC-MS: tR=2.88 min, [M+1]+=320.19, [M−1]−=318.02.

Workup

  1. stirringthe mixture was stirred at rt for 16 h
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in water (150 ml)
  4. extractionextracted twice with diethyl ether (150 ml)
  5. customThe solid that separated
  6. customwas collected
  7. washwashed with water
  8. customevaporated twice from EA
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-c7258cdcfc7c44909a8bab2d91687812
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Reaction notes

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