Water → HCID 58914751, compound

HRID 1297801Notes

Reaction equation

HRID 1297801 reaction equation
[C:1]([Si:5]([CH3:42])([CH3:41])[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2([C:24]3[CH:29]=[C:28]([CH3:30])[C:27]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])=[C:26]([CH3:39])[CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])=[CH:9][C:8]=1[CH3:40])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[Cl:49][C:50]1[N:55]=[C:54](Cl)[CH:53]=[CH:52][N:51]=1.O>C1COCC1.C(OCC)C>[C:1]([Si:5]([CH3:42])([CH3:41])[O:6][C:7]1[C:8]([CH3:40])=[CH:9][C:10]([C:14]2([C:24]3[CH:29]=[C:28]([CH3:30])[C:27]([O:31][Si:32]([C:35]([CH3:36])([CH3:38])[CH3:37])([CH3:33])[CH3:34])=[C:26]([CH3:39])[CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:52]3[CH:53]=[CH:54][N:55]=[C:50]([Cl:49])[N:51]=3)[C:15]2=[O:23])=[CH:11][C:12]=1[CH3:13])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 775312,4-DichloropyrimidineHCID 23665647Potassium tert-butoxideHCID 58914719HCID 58914719, compound

Product 1

HCID 58914751HCID 58914751, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an N2 atmosphere, dissolve 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (0.519 g, 0.862 mmol) in dry THF (2 mL). Cool the reaction to 0° C. Add a solution of potassium t-butoxide (1.0 M) in THF (0.95 mL). Allow the reaction to stir at 0° C. for 10 minutes. Add 2,4-dichloro-pyrmidine (0.141 g, 0.948 mmol), and remove the ice bath. Heat the reaction to 55° C. and stir overnight. Dilute the reaction with water (200 mL) and diethyl ether (200 mL). Separate the layers and wash the aqueous layer with diethyl ether (100 mL). Combine the organic layers. Dry the organic layer with sodium sulfate and concentrate in vacuo. Purify the crude oil by flash column chromatography. Elute the column with 20% ethyl acetate in hexanes to give 0.289 g (47%) of the title compound: 1H NMR(DMSO-d6); δ8.60 (d, 1H), 8.41 (d, 1H), 8.28 (d, 1H), 7.41-7.38 (m, 1H), 7.25-7.22 (m, 1H), 7.17-7.14 (m, 1H), 6.78 (s, 4H), 2.11 (s, 12H), 1.00 (s, 18H), 0.15 (s, 6H), 0.15 (s, 6H).

Workup

  1. temperatureCool
  2. customthe reaction to 0° C
  3. customthe reaction
  4. temperatureHeat
  5. customthe reaction to 55° C.
  6. stirringstir overnight
  7. additionDilute
  8. customSeparate the layers
  9. washwash the aqueous layer with diethyl ether (100 mL)
  10. dry with materialDry the organic layer with sodium sulfate
  11. concentrationconcentrate in vacuo
  12. customPurify the crude oil by flash column chromatography
  13. washElute the column with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-fd90b3e4fa5743799a7fd2f4dbc5d140
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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