Toluene → HCID 11662049, compound

HRID 1432172Notes

Reaction equation

HRID 1432172 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[C:9]3[C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=4[S:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:3][CH2:2]1.[F:21][C:22]1[CH:23]=[C:24]([CH2:28][C:29](C2C=CC=CC=2)=O)[CH:25]=[CH:26][CH:27]=1.[C-:37]#[N:38].C([Al+]CC)C.C1(C)C=CC=CC=1>C(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:21][C:22]1[CH:23]=[C:24]([C:28]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8]3[C:9]4[C:16]5[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=5[S:14][C:10]=4[N:11]=[CH:12][N:13]=3)[CH2:5][CH2:6]2)([CH3:29])[C:37]#[N:38])[CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 27590612-(3-fluorophenyl)-1-phenylethanoneHCID 16686413Diethyl aluminum cyanideHCID 22182391HCID 22182391, compound

Product 1

HCID 11662049HCID 11662049, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(piperidin-4-yl)-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-amine (2.86 g, 10 mmol) and 3-fluorophenylacetophenone (1.38 g, 10 mmol) in dry DCM (25 mL) was added titanium isopropoxide (2.85 g, 10 m.mol) at room temperature and stirred for 24 h. 1 M solution of diethylaluminumcyanide in toluene (1.2 mL, 10 mmol) was added to the above solution and the mixture was allowed to stir for 24 h. The reaction was quenched by the addition of saturated aq. NaHCO3 solution (15 mL) and the organic layer was separated, dried and concentrated under reduced pressure to get the title compound (4.3 g, 100%) as pale yellow powder. 1H NMR (400 MHz, CDCl3): δ 8.01 (s, 1H), 7.35-7.24 (m, 2H), 6.99 (t, 1H), 6.78 (t, 1H), 4.21 (brs, 1H, NH), 3.91-3.86 (m, 1H), 3.11-3.03 (m, 2H), 2.91 (t, 2H), 2.49-2.27 (m, 4H), 2.00-1.92 (m, 4H), 1.42 (s, 3H). MS (ESI) m/z: Calculated: 435.56; Observed: 436.2 (M++1).

Workup

  1. stirringto stir for 24 h
  2. customThe reaction was quenched by the addition of saturated aq. NaHCO3 solution (15 mL)
  3. customthe organic layer was separated
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-173623c9286f44e1a171a3bd33e6f443
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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