Lithium Hydroxide → HCID 121317891, compound

HRID 58187Notes

Reaction equation

HRID 58187 reaction equation
[OH-].[Li+].[C:3]([O:7][C:8]([N:10]([C:24]1[CH:29]=[C:28]([N:30]([CH3:53])[C:31]([N:33]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:34]2[C:39]([Cl:40])=[C:38]([O:41][CH3:42])[CH:37]=[C:36]([O:43][CH3:44])[C:35]=2[Cl:45])=[O:32])[N:27]=[CH:26][N:25]=1)[C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])=[O:9])([CH3:6])([CH3:5])[CH3:4].CCOC(C)=O.CCCCCC>C1COCC1.O>[C:3]([O:7][C:8]([N:10]([C:24]1[CH:29]=[C:28]([N:30]([CH3:53])[C:31]([N:33]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:34]2[C:39]([Cl:40])=[C:38]([O:41][CH3:42])[CH:37]=[C:36]([O:43][CH3:44])[C:35]=2[Cl:45])=[O:32])[N:27]=[CH:26][N:25]=1)[C:11]1[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])=[O:9])([CH3:4])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 21226206Ethyl acetate hexaneHCID 118029281Methyl 4-((tert-butoxycarbonyl)(6-(3-(tert-butoxycarbonyl)-3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methylureido)pyrimidin-4-yl)amino)-3-nitrobenzoate

Product 1

HCID 121317891HCID 121317891, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.08 g, 2.99 mmol) was added to a solution of methyl 4-((tert-butoxycarbonyl)(6-(3-(tert-butoxycarbonyl)-3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methylureido)pyrimidin-4-yl)amino)-3-nitrobenzoate (1.5 g, 1.997 mmol) (Procedure 2J, Step c) in a mixture of THF (10 mL) and water (2 mL) at 0° C. The resulting reaction mixture was allowed to warm to room temperature and stirred for 5 h. After completion of the reaction by TLC (EtOAc:Hexane 3:7), the reaction mixture was concentrated under vacuum to get a crude residue. The crude residue was dissolved in water and extracted with ether (3×30 mL). The aqueous layer was acidified with 10% citric acid solution and the precipitated solid was filtered, washed with cold water and dried in vacuo to afford the title compound (1.3 g, yield: 93%) as a light brown solid. MS (ESI): 737.2 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. customto get a crude residue
  4. extractionextracted with ether (3×30 mL)
  5. filtrationthe precipitated solid was filtered
  6. washwashed with cold water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-420844f458d84f87ba3e340bb7c3984f
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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