Dimethylformamide → HCID 178516344, compound

HRID 1890458Notes

Reaction equation

HRID 1890458 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]([CH2:14][C:15]([O-])=O)[NH:10][C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na+].CN(C)C=O.Cl.CN(C)CCCN=C=NCC.[Br:36][C:37]1[CH:38]=[C:39]([NH2:44])[C:40]([NH2:43])=[CH:41][CH:42]=1>C(OCC)(=O)C.N1C=CC=CC=1>[Br:36][C:37]1[CH:42]=[CH:41][C:40]2[NH:43][C:15]([CH2:14][C:9]3[NH:10][C:11](=[O:13])[CH:12]=[C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[N:8]=3)=[N:44][C:39]=2[CH:38]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 3235934-Bromobenzene-1,2-diamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 178516344HCID 178516344, compoundYield 28.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a round-bottomed flask, 1.3 g of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate are introduced into 10 ml of dimethylformamide and then 10 ml of pyridine, 1.44 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 1.87 g of 4-bromobenzene-1,2-diamine are added. The reaction mixture is stirred at ambient temperature overnight and is then concentrated to dryness under reduced pressure. The residue is taken up in 40 ml of acetic acid and brought to reflux for 4 hours, then concentrated under reduced pressure. 100 ml of water are then added and a saturated aqueous solution of sodium bicarbonate is added until a pH in the region of 7 is obtained. 200 ml of ethyl acetate are then added and the resulting mixture is stirred for 1 hour. The precipitate formed is filtered then purified by silica gel column chromatography, elution being carried out with a gradient of the eluent CH2Cl2/MeOH: 80/20 in dichloromethane of 0% to 100% in 25 minutes. 560 mg of 2-[(5-bromo-1H-benzimidazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of an off-white solid, the characteristics of which are the following:

Workup

  1. concentrationis then concentrated to dryness under reduced pressure
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated under reduced pressure
  4. addition100 ml of water are then added
  5. additiona saturated aqueous solution of sodium bicarbonate is added until a pH in the region of 7
  6. customis obtained
  7. stirringthe resulting mixture is stirred for 1 hour
  8. customThe precipitate formed
  9. filtrationis filtered
  10. customthen purified by silica gel column chromatography, elution
  11. wait80/20 in dichloromethane of 0% to 100% in 25 minutes

Sources & evidence

ORD record
ord-e0f2fe73fbc24f0881ce51b7657789d2
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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