Triacetoxyperiodinane → (4-fluorophenyl)(7-hydroxy-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone

HRID 1424437Notes

Reaction equation

HRID 1424437 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:27])[C:9]2[N:18]=[C:17]([NH:19][C:20]3[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=3)[C:16]3[C:11](=[CH:12][C:13]([OH:26])=[CH:14][CH:15]=3)[N:10]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CS(C)=O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:9]2[N:18]=[C:17]([NH:19][C:20]3[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=3)[C:16]3[C:11](=[CH:12][C:13]([OH:26])=[CH:14][CH:15]=3)[N:10]=2)=[O:27])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 1358951832-((4-fluorophenyl)(hydroxy)methyl)-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-7-ol

Product 1

HCID 135895184(4-fluorophenyl)(7-hydroxy-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanoneYield 14%

Reagents, catalysts & solvents 1

HCID 21912085Dimethylsulfoxide-dichloromethaneSolvent

Procedure

To 2-((4-fluorophenyl)(hydroxy)methyl)-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-7-ol (50 mg, 0.14 mmol) in 1:3 DMSO/DCM was added Dess-Martin periodinane (81 mg, 0.19 mmol) in one portion. After stirring for 1 h at rt, the solution was cooled to 0° C. and quenched by addition of a 1:1 mixture of 10% sodium thiosulfate pentahydrate and saturated sodium bicarbonate. The resulting dark precipitate was collected and chromatographed on silica eluting with 2 to 10% MeOH/DCM. Trituration of the colored solid with MeOH afforded (4-fluorophenyl)(7-hydroxy-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone as a white solid (7 mg, 14%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.27 (s, 3H), 6.47 (bs, 1H), 7.06 (m, 2H), 7.13 (m, 1H), 7.38 (m, 2H), 8.06 (m, 2H), 8.57 (m, 2H), 10.41 (bs, 1H), 10.60 (bs, 1H), 12.15 (bs, 1H). LC-MS (ESI) m/z 364 (M+H)+.

Workup

  1. temperaturethe solution was cooled to 0° C.
  2. customquenched by addition of a 1:1 mixture of 10% sodium thiosulfate pentahydrate and saturated sodium bicarbonate
  3. customThe resulting dark precipitate was collected
  4. customchromatographed on silica eluting with 2 to 10% MeOH/DCM

Sources & evidence

ORD record
ord-dc458ccdb94e423f9e32d39e89f5d291
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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