tert-Butyl hydroperoxide → HCID 86603178, compound

HRID 1818949Notes

Reaction equation

HRID 1818949 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[S:16][C:15]3[C:14]([NH:17][CH2:18][CH2:19][C:20]4[S:24][C:23]([NH:25][C:26]([NH:28][C:29]5C=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=5)=[O:27])=[N:22][CH:21]=4)=[N:13][CH:12]=[N:11][C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=NN=N1.C(N(CC)[P:47]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])C.C([O:64]O)(C)(C)C.OS([O-])=O.[Na+]>C1COCC1.CC#N>[F:36][C:35]([F:38])([F:37])[C:31]([CH:32]=[CH2:33])=[CH:30][CH2:29][NH:28][C:26](=[O:27])[NH:25][C:23]1[S:24][C:20]([CH2:19][CH2:18][NH:17][C:14]2[C:15]3[S:16][C:8]([C:4]4[CH:3]=[C:2]([O:1][P:47](=[O:64])([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])[O:53][C:54]([CH3:55])([CH3:56])[CH3:57])[CH:7]=[CH:6][CH:5]=4)=[CH:9][C:10]=3[N:11]=[CH:12][N:13]=2)=[CH:21][N:22]=1

Participants

8

Reactant 5

HCID 6410tert-Butyl hydroperoxideHCID 4251849Di-tert-butyl diethylphosphoramiditeHCID 23665763Sodium BisulfiteHCID 57886516HCID 57886516, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 86603178HCID 86603178, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 57.1 (0.20 mmol) in THF (20 mL) was added 1-H-tetrazole (6.0 mL of a 3% w/w in CH3CN). The reaction was purged with nitrogen and di-tert-butyl diethylphosphoramidite (1.06 mmol) was added. After stirring at room temperature for 3.5 hours, tert-butyl hydroperoxide (5 mL of 70% aqueous solution) was added. After stirring for 1 hour, the reaction was cooled to 0° C. followed by the addition of NaHSO3 (15 mL of a 5% aqueous solution). After an additional 1 hour, the reaction mixture was extracted with dichloromethane, washed with brine, dried and concentrated to give phosphoric acid di-tert-butyl ester 3-[4-(2-{2-[3-(3-trifluoromethyl-penta-2,4-dienyl)-ureido]-thiazol-5-yl}-ethylamino)-thieno[3,2-d]pyrimidin-6-yl]-phenyl ester (compound 57.2)

Workup

  1. additionwas added
  2. stirringAfter stirring for 1 hour
  3. temperaturethe reaction was cooled to 0° C.
  4. waitAfter an additional 1 hour
  5. extractionthe reaction mixture was extracted with dichloromethane
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4c127a5c996a41f694f0e9d9fa4a1ac3
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

Loading…