Water → 3-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-[6-(2-nitro-phenylamino)pyrimidin-4-yl]1-pyridin-3-ylmethyl-urea

HRID 58131Notes

Reaction equation

HRID 58131 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[C:15]([NH:17][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:14]=[CH:13][N:12]=1)([O-:3])=[O:2].[H-].[Na+].[Cl:27][C:28]1[C:33]([N:34]=[C:35]=[O:36])=[C:32]([Cl:37])[C:31]([O:38][CH3:39])=[CH:30][C:29]=1[O:40][CH3:41].O>C1COCC1>[Cl:27][C:28]1[C:29]([O:40][CH3:41])=[CH:30][C:31]([O:38][CH3:39])=[C:32]([Cl:37])[C:33]=1[NH:34][C:35](=[O:36])[N:17]([C:15]1[CH:16]=[C:11]([NH:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[N:12]=[CH:13][N:14]=1)[CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 860869932,6-Dichloro-3,5-dimethoxyphenyl isocyanateHCID 118024538N-(2-Nitro-phenyl)-N'-pyridin-3-ylmethyl-pyrimidine-4,6-diamine

Product 1

HCID 1180249403-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-[6-(2-nitro-phenylamino)pyrimidin-4-yl]1-pyridin-3-ylmethyl-ureaYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-nitro-phenyl)-N′-pyridin-3-ylmethyl-pyrimidine-4,6-diamine (150 g, 0.467 mmol) in THF (15 mL) was added NaH (60%, 48 g, 1.2 mmol) at 0° C., and the mixture was stirred for 30 minutes at room temperature. A solution of 2,4-dichloro-3-isocyanato-1,5-dimethoxy-benzene (procedure 2A, steps a-d; 180 g, 0.73 mmol) was added dropwise at room temperature. The resulting mixture was stirred for 2 hours. Water (2 mL) was added to quench the reaction. The mixture was concentrated, and the residue was purified by flash chromatography on silica to obtain the title compound (85 mg, yield: 32%). MS (ESI): 570 [M+H]+.

Workup

  1. stirringThe resulting mixture was stirred for 2 hours
  2. customto quench
  3. customthe reaction
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-4257a1978a544079a17cda17ca187a4e
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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