HCID 10321280, compound → HCID 10364131, compound

HRID 2216994Notes

Reaction equation

HRID 2216994 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH:9]([N:11]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:12]([NH:14][C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])=[O:13])[CH3:10])=[CH:4][N:3]=1.CC(C)([O-])C.[K+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[N:14]([C@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[C:12](=[O:13])[N:11]([C:23]3[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[CH:9]([CH3:10])[C:5]2=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 10321280HCID 10321280, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10364131HCID 10364131, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 1-[1-(2,4-dichloro-pyrimidin-5-yl)-ethyl]-1-(4-methoxy-phenyl)-3-[1-(S)-phenyl-ethyl]-urea (less polar diastereomer, 250 mg, 0.56 mmol) (from Example 16 supra) in tetrahydrofuran (5 mL). cooled to 5° C. was treated with potassium tert-butoxide (1.0 M solution in tetrahydrofuran, 0.62 mL, 0.62 mmol). After stirring at 5° C. for 15 minutes and then at room temperature for another 15 minutes, reaction mixture was diluted with ethyl acetate (20 mL) and was washed with water (2×10 mL) and dried over MgSO4. Solvent was evaporated under reduced pressure to give crude 7-chloro-3-(4-methoxy-phenyl)-4-methyl-1-[1-(S)-phenyl-ethyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one which was used directly in the following step. (308 mg, contains some solvent).

Workup

  1. waitat room temperature for another 15 minutes
  2. customreaction mixture
  3. washwas washed with water (2×10 mL)
  4. dry with materialdried over MgSO4
  5. customSolvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f6305bdfba584f8ab4d30758ce5d056f
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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