Toluene → HCID 178432669, compound

HRID 129023Notes

Reaction equation

HRID 129023 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH3:50])[C:5]2[CH2:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]4[N:30](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:29]=[N:28][N:27]=4)=[CH:16][CH:15]=3)[C:6]=2[N:7]=1.C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1(C)C=CC=CC=1.C(C(O)=[O:73])(F)(F)F.[OH-].[Na+]>C1COCC1.O>[CH3:1][C:2]1[N:3]=[C:4]([CH3:50])[C:5]2[CH2:11][CH:10]([OH:73])[C:9](=[O:12])[N:8]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]4[NH:30][N:29]=[N:28][N:27]=4)=[CH:18][CH:19]=3)[C:6]=2[N:7]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 19372993HCID 19372993, compound

Product 1

HCID 178432669HCID 178432669, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

To a cooled (-78° C.) solution of 2,4-dimethyl-8-[2'-(1-triphenylmethyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one (1.57 g, 2.41 mmol) in THF (5 mL) was added 0.5M potassium hexamethyldisilazide in toluene (5.5 mL, 2.75 mmol). After 45 min, a solution of (+)-camphorsulfonyloxaziridine in THF (5 mL) was added. The mixture was allowed to warm to 5° C. over 5 h. Water (2 mL) and CF3CO2H (2 mL) were added and stirring was continued for 1 h. 1N NaOH (30 mL) was added and the mixture was extracted with EtOAc (discarded). The aqueous phase was acidified to pH 4 with 1N HCl and extracted with CHCl3. The extracts were dried MgSO4) and concentrated. Purification by flash chromatography (5-10% MeOH/CHCl3) gave 377 mg of a yellow oil. Crystallization from acetone yielded 234 mg (23%) of product as an off-white solid, mp 154°-156° C.

Workup

  1. waitwas continued for 1 h
  2. extractionthe mixture was extracted with EtOAc (discarded)
  3. extractionextracted with CHCl3
  4. concentrationconcentrated
  5. customPurification by flash chromatography (5-10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-ba074e7d655f4af998219ea9c3bf80cb
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Reaction notes

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