Benzoyl chloride → 2-(2-Benzoylamino-pyrimidin-4-yl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 1180094Notes

Reaction equation

HRID 1180094 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[NH:14][C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[N:18]=3)=[CH:16][C:10]=2[C:9]1=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[C:32]1([C:38](Cl)=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[NH:14][C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:38](=[O:39])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:18]=3)=[CH:16][C:10]=2[C:9]1=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 247769152-(2-Amino-pyrimidin-4-yl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 247766742-(2-Benzoylamino-pyrimidin-4-yl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(2-Amino-pyrimidin-4-yl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester and Et3N (4 eq.) in dry THF, PhCOCl (2 eq.) was added and the mixture was stirred at room temperature under argon overnight. Thus NaOH(1N) was added; after 30′ the solvent was evaporated and the residue was dissolved in water and the aqueous phase was extracted with AcOEt (2×). The organic phase was then washed with aq. NH4Cl and dried over Na2SO4. After solvent evaporation the crude product was purified by flash chromatography (CH2Cl2:MeOH 97:3) to give the pure product as a solid.

Workup

  1. additionwas added
  2. customafter 30′ the solvent was evaporated
  3. dissolutionthe residue was dissolved in water
  4. extractionthe aqueous phase was extracted with AcOEt (2×)
  5. washThe organic phase was then washed with aq. NH4Cl
  6. dry with materialdried over Na2SO4
  7. customAfter solvent evaporation the crude product
  8. customwas purified by flash chromatography (CH2Cl2:MeOH 97:3)

Sources & evidence

ORD record
ord-777e9db7ae81486aa8e0dd0c3ebe6d62
Source dataset
uspto-grants-2007_10
Patent number
US07279575B2

Reaction notes

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