Aluminium lithium hydride → 2-[(5-Fluoro-2-{[4-(hydroxymethyl)phenyl]amino}-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide

HRID 1864076Notes

Reaction equation

HRID 1864076 reaction equation
[F:1][C:2]1[C:3]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([NH:29][CH:30]([CH3:32])[CH3:31])=[O:28])=[N:4][C:5]([NH:8][C:9]2[CH:19]=[CH:18][C:12]([C:13](OCC)=[O:14])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[C:3]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([NH:29][CH:30]([CH3:32])[CH3:31])=[O:28])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:13][OH:14])=[CH:18][CH:19]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57974136Ethyl 4-({5-fluoro-4-[(2-{[(1 methylethyl)amino]carbonyl}phenyl)amino]-2 pyrimidinyl}amino)benzoate

Product 1

HCID 579742112-[(5-Fluoro-2-{[4-(hydroxymethyl)phenyl]amino}-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamideYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-({5-fluoro-4-[(2-{[(1methylethyl)amino]carbonyl}phenyl)amino]-2-pyrimidinyl}amino)benzoate (1.47 g, 3.36 mmol) in THF (80 mL) was slowly added a solution of LiAlH4 (1.0M solution, 3.0 eq) at 0° C. After the addition was complete, the reaction mixture was slowly warmed up to room temperature and stirred for 16 h. The reaction mixture was quenched with 15 mL of 1.0 M Rochelle's solution. The water phase was extracted by EtOAc (2×30 mL) and the combined organic phases were washed by brine (3×30 mL) then dried over Na2SO4. The solvent was evaporated to produce a solid, which was washed with hexane (3×30 mL), then dried in vacuo to give the desired product. (1.15, 87% yield). MS: M(C21H22FN5O2)=395.44, (M+H)+=396

Workup

  1. additionAfter the addition
  2. customThe reaction mixture was quenched with 15 mL of 1.0 M Rochelle's solution
  3. extractionThe water phase was extracted by EtOAc (2×30 mL)
  4. washthe combined organic phases were washed by brine (3×30 mL)
  5. dry with materialthen dried over Na2SO4
  6. customThe solvent was evaporated
  7. customto produce a solid, which
  8. washwas washed with hexane (3×30 mL)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-608b68e470004833bf433461510b0a93
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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