Tributylphosphine → HCID 59351578, compound

HRID 1889434Notes

Reaction equation

HRID 1889434 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:11](=[O:12])[C:10]2[CH:13]=[C:14]([CH2:16][CH3:17])[S:15][C:9]=2[NH:8][C:7]1=[O:18].[F:25][C:26]1[CH:27]=[C:28]([C:35]2[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:29]=[C:30]([F:34])[C:31]=1[CH2:32]O.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C(OCC)(=O)C.O1CCCC1>[CH2:16]([C:14]1[S:15][C:9]2[N:8]([CH2:32][C:31]3[C:26]([F:25])=[CH:27][C:28]([C:35]4[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=4)=[CH:29][C:30]=3[F:34])[C:7](=[O:18])[NH:6][C:11](=[O:12])[C:10]=2[CH:13]=1)[CH3:17]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 593517753-(2,4-dimethoxybenzyl)-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneHCID 67529845HCID 67529845, compound

Product 1

HCID 59351578HCID 59351578, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(2,4-dimethoxybenzyl)-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (2 g), 3′,5′-difluoro-4′-(hydroxymethyl)biphenyl-2-carbonitrile (1.6 g), 1,1′-(azodicarbonyl)dipiperidine (2.2 g), tributylphosphine (2.2 mL) and tetrahydrofuran (4 mL) was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in trifluoroacetic acid (15 mL), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was concentrated under reduced pressure. To the obtained residue was added ethyl acetate, and insoluble material was filtered off. The filtrate was concentrated and recrystallized from diethyl ether to give the title compound as a colorless solid (1.5 g, 76%).

Workup

  1. washwashed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionThe obtained residue was dissolved in trifluoroacetic acid (15 mL)
  5. stirringthe mixture was stirred at 50° C. for 2 hr
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. additionTo the obtained residue was added ethyl acetate, and insoluble material
  8. filtrationwas filtered off
  9. concentrationThe filtrate was concentrated
  10. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-c01d29e2260e454a8891c7266344d93c
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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