Diisopropylethylamine → N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine

HRID 971226Notes

Reaction equation

HRID 971226 reaction equation
ClC(OC(Cl)C)=O.C([N:15]1[CH2:24][CH2:23][C:22]2[C:21]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[N:20][C:19]([S:36][CH3:37])=[N:18][C:17]=2[CH2:16]1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C>ClCCCl>[F:34][C:32]([F:33])([F:35])[C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:21]2[C:22]3[CH2:23][CH2:24][NH:15][CH2:16][C:17]=3[N:18]=[C:19]([S:36][CH3:37])[N:20]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 590215717-benzyl-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine

Product 1

HCID 59021576N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amineYield 66.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Chloroethyl chloroformate (572 mg, 4 mmol) was added dropwise to a mixture of 7-benzyl-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine (860 mg, 2 mmol) and diisopropylethyl amine (516 mg, 4 mmol) in 1,2-dichloroethane (5 mL, anhydrous) at 0° C. After addition, the reaction mixture was stirred at room temperature for 1 hr. Solvent was removed in vacuo, residue was dissolved in methanol (10 mL) and was stirred at room temperature overnight. Solvent was removed in vacuo, residue was dissolved in ethyl acetate and was washed with saturated aqueous sodium bicarbonate, brine and dried over sodium sulfate. Solvent was removed in vacuo and residue was triturated with diethyl ether to yield the product as a beige solid (454 mg).

Workup

  1. additionAfter addition
  2. customSolvent was removed in vacuo, residue
  3. dissolutionwas dissolved in methanol (10 mL)
  4. stirringwas stirred at room temperature overnight
  5. customSolvent was removed in vacuo, residue
  6. dissolutionwas dissolved in ethyl acetate
  7. washwas washed with saturated aqueous sodium bicarbonate, brine
  8. dry with materialdried over sodium sulfate
  9. customSolvent was removed in vacuo and residue
  10. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-4f2147e437334650be6e706c6640597c
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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