4-Methoxy-o-phenylenediamine → HCID 136041750, compound

HRID 1890459Notes

Reaction equation

HRID 1890459 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+].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[NH2:28]>>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]2[N:19]=[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)[NH:28][C:21]=2[CH:22]=1

Participants

3

Reactant 2

HCID 1534044-Methoxy-o-phenylenediamineHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136041750HCID 136041750, compoundYield 2.3%

Procedure

The product is prepared according to the procedure described in Stage 3 of Example 1, using 261 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate and 166 mg of 1,2-diamino-4-methoxybenzene in place of the 1,2-diamino-4-fluorobenzene. After purification by silica gel column chromatography, elution being carried out with a gradient of pure CH2Cl2 to CH2Cl2/MeOH: 85/15, 8 mg of 2-[(6-methoxy-1H-benzimidazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one being obtained in the form of an off-white solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter purification
  3. washby silica gel column chromatography, elution

Sources & evidence

ORD record
ord-fefb6abeebed414f83e6d695fcb956eb
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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