Ammonia → (R)-1-(2-chloro-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-ylamino)-1-(4-fluoro-phenyl)-2-methyl-propan-2-ol

HRID 70090Notes

Reaction equation

HRID 70090 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:11][C@H:12]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:13]([CH3:16])([OH:15])[CH3:14])[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[OH:24]O.N>C(O)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:11][C@H:12]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[C:13]([CH3:16])([OH:15])[CH3:14])[C:5]2[S:10](=[O:24])[CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 59708405(R)-1-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-1-(4-fluorophenyl)-2-methylpropan-2-ol

Product 1

HCID 59708370(R)-1-(2-chloro-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-ylamino)-1-(4-fluoro-phenyl)-2-methyl-propan-2-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

300 mg (R)-1-(2-chloro-6,7-dihydro-thieno[3,2-d]pyrimidin-4-ylamino)-1-(4-fluoro-phenyl)-2-methyl-propan-2-ol are placed in 2.0 ml acetic acid. The reaction mixture is cooled to +10° C. 127 μl hydrogen peroxide (35%) are added dropwise. The reaction mixture is stirred for 1 hour at +10° C. and then stirred into ice water. It is then made basic with an ammonia solution. The precipitate formed is suction filtered and purified by chromatography (silica gel, petroleum ether/ethyl acetate 50/50 to 0/100 then ethyl acetate/methanol 50/50). 70 mg of the product are obtained as an oil. Analytical HPLC-MS (method D): RT=1.17 min.

Workup

  1. temperatureThe reaction mixture is cooled to +10° C
  2. customThe precipitate formed
  3. filtrationfiltered
  4. custompurified by chromatography (silica gel, petroleum ether/ethyl acetate 50/50 to 0/100

Sources & evidence

ORD record
ord-565ddd56db364e90a7e8f073eeeaa138
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Reaction notes

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