Water → N-{3-[7-(3-tert-butyl-ureido)-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-6-yl]-2,4-dichloro-phenyl}-3-trifluoromethyl-benzamide

HRID 252196Notes

Reaction equation

HRID 252196 reaction equation
[NH2:1][C:2]1[C:3]([C:14]2[C:15]([Cl:34])=[C:16]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH:17]=[CH:18][C:19]=2[Cl:20])=[CH:4][C:5]2[CH:10]=[N:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[N:13]=1.[H-].[Na+].[C:37]([N:41]=[C:42]=[O:43])([CH3:40])([CH3:39])[CH3:38].O>CN(C=O)C>[C:37]([NH:41][C:42](=[O:43])[NH:1][C:2]1[C:3]([C:14]2[C:15]([Cl:34])=[C:16]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH:17]=[CH:18][C:19]=2[Cl:20])=[CH:4][C:5]2[CH:10]=[N:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[N:13]=1)([CH3:40])([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 62412tert-Butyl isocyanateHCID 59833927HCID 59833927, compound

Product 1

HCID 59860301N-{3-[7-(3-tert-butyl-ureido)-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-6-yl]-2,4-dichloro-phenyl}-3-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N—[3-(7-amino-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-6-yl)-2,4-dichloro-phenyl]-3-trifluoromethyl-benzamide (700 mg, 1.34 mmol) in dry DMF (10 ml) at 0° C. is added NaH (60% oil suspension, 64 mg, 1.6 mmol) slowly. The reaction mixture is stirred at room temperature for 30 minutes and then to this reaction mixture t-butyl-isocyanate (0.19 ml, 1.6 mmol) is added. The reaction is stirred at room temperature for 5 hours. The reaction mixture is diluted into 100 ml water, extracted with 80 ml ethyl acetate three times. The organic phase is combined and washed with brine, dried over Na2SO4. The crude product is purified by flash silica gel column to give the title compound as light yellow solid.

Workup

  1. stirringThe reaction is stirred at room temperature for 5 hours
  2. extractionextracted with 80 ml ethyl acetate three times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product is purified by flash silica gel column

Sources & evidence

ORD record
ord-98ee21a0102a470a94288c606ca82a76
Source dataset
uspto-grants-2011_01
Patent number
US07868018B2

Reaction notes

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