Water → 5-{1-tert-Butyl-2-[5-methoxy-2-(3-methyl-1,2,4-thiadiazol-5-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine

HRID 1966705Notes

Reaction equation

HRID 1966705 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:19])[C:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][N:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:30]2[S:34][N:33]=[C:32]([CH3:35])[N:31]=2)=[C:26]([CH:29]=1)[CH:27]=O.O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:15]([N:14]1[C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=3)=[CH:9][C:10]=2[N:19]=[C:27]1[C:26]1[CH:29]=[C:22]([O:21][CH3:20])[CH:23]=[CH:24][C:25]=1[C:30]1[S:34][N:33]=[C:32]([CH3:35])[N:31]=1)([CH3:16])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamineHCID 585420075-Methoxy-2-(3-methyl-1,2,4-thiadiazol-5-yl)-benzaldehyde

Product 1

HCID 532394275-{1-tert-Butyl-2-[5-methoxy-2-(3-methyl-1,2,4-thiadiazol-5-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamineYield 20%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (110 mg, 0.43 mmol) and 5-methoxy-2-(3-methyl-1,2,4-thiadiazol-5-yl)-benzaldehyde (100 mg, 0.43 mmol) in acetic acid (5 mL) is warmed to 50° C. for 12 hours then at 80° C. for 60 hours. The reaction mixture is cooled to room temperature and poured into water and NaHCO3 (sat.). The product is extracted into EtOAc (3×) and the combined organics are dried (MgSO4), filtered and concentrated. Purification via flash chromatography (12 g silica gel, 0-5% MeOH/CH2Cl2) affords the title compound (40 mg, 20%). LCMS (ESMS): m/z 472.20 (M++1)

Workup

  1. extractionThe product is extracted into EtOAc (3×)
  2. dry with materialthe combined organics are dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography (12 g silica gel, 0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0f697a1e8cee44f59d94af434aa21860
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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