Trifluoroacetic acid → 2-(Tetrahydropyran-4-ylamino)-6-[(2-fluorophenyl)methyl]thieno[2,3-d]pyrimidine

HRID 9762Notes

Reaction equation

HRID 9762 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH:16]=[C:15]([CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[F:25])O)[S:14][C:12]=3[N:13]=2)[CH2:3][CH2:2]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[O:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH:16]=[C:15]([CH2:17][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[F:25])[S:14][C:12]=3[N:13]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 101723842-(Tetrahydropyran-4-ylamino)-6-[(2-fluorophenyl)hydroxylmethyl]thieno[2,3-d]pyrimidine

Product 1

HCID 102153852-(Tetrahydropyran-4-ylamino)-6-[(2-fluorophenyl)methyl]thieno[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The alcohol (140 mg) obtained in Example 2A was stirred with triethylsilane (1.0 mL) and trifluoroacetic acid (1.5 mL) in dichloromethane (5 mL) for 4 hours. The solvents were removed. The residue was diluted with toluene (5 mL) and then concentrated. This dilution-concentration process was repeated three times. Purification with preparative TLC (50% EtOAc/Hexanes) gave the final product. It was converted to the hydrochloride salt with 1N HCl in ether to yield 65 mg of the salt. MP: 217–219° C. MS: 344 (M+H).

Workup

  1. customThe solvents were removed
  2. additionThe residue was diluted with toluene (5 mL)
  3. concentrationconcentrated
  4. customPurification with preparative TLC (50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-812a26b6b0914c49893210dc67586be6
Source dataset
uspto-grants-2006_08
Patent number
US07091347B2

Reaction notes

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