N-Methyl-o-phenylenediamine → 2-[(1-Methyl-1H-benzimidazol-2-yl)methyl]-6-(4-morpholinyl)-4(1H)-pyrimidinone

HRID 1890468Notes

Reaction equation

HRID 1890468 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+].[CH3:19][NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH2:27]>>[CH3:19][N:20]1[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:27]=[C:15]1[CH2:14][C:9]1[NH:10][C:11](=[O:13])[CH:12]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[N:8]=1

Participants

3

Reactant 2

HCID 78498N-Methyl-o-phenylenediamineHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 1355666442-[(1-Methyl-1H-benzimidazol-2-yl)methyl]-6-(4-morpholinyl)-4(1H)-pyrimidinoneYield 60.2%

Procedure

The product is prepared according to the procedure described in Example 3, using 300 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate and 280 mg of N-methyl-1,2-phenylenediamine in place of the 4-bromobenzene-1,2-diamine. After purification by silica column chromatography, eluent: a gradient of the pure CH2Cl2 eluent to CH2Cl2/MeOH: 90/10, 225 mg of 2-[(1-methyl-1H-benzimidazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter purification by silica column chromatography, eluent

Sources & evidence

ORD record
ord-be459157853e43aea2bf392394bebc83
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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