Butyl ether → HCID 11582641, compound

HRID 1432173Notes

Reaction equation

HRID 1432173 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]3[C:20]4[C:27]5[CH2:28][CH2:29][CH2:30][CH2:31][C:26]=5[S:25][C:21]=4[N:22]=[CH:23][N:24]=3)[CH2:14][CH2:13]2)([CH3:11])[C:9]#N)[CH:5]=[CH:6][CH:7]=1.C[Mg+].[Br-].C(OCCCC)CCC.[NH4+].[Cl-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]([N:12]2[CH2:13][CH2:14][CH:15]([NH:18][C:19]3[C:20]4[C:27]5[CH2:28][CH2:29][CH2:30][CH2:31][C:26]=5[S:25][C:21]=4[N:22]=[CH:23][N:24]=3)[CH2:16][CH2:17]2)([CH3:11])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8909Butyl etherHCID 25517Ammonium ChlorideHCID 11662049HCID 11662049, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 11582641HCID 11582641, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Fluorophenyl)-2-(4-(5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl amino)piperidin-1-yl)propanenitrile (435 mg, 1 mmol) was dissolved in dry THF (20 mL) and was added 1 M solution of MeMgBr in butyl ether (1.7 mL, 12 mmol) at 0° C. The reaction was stirred at room temperature for 3 h. The mixture was poured into a cold saturated NH4Cl solution (10 mL) and extracted with DCM (2×25 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4 and evaporated under reduced pressure. Purification by silica chromatography (2% MeOH-DCM) afforded the title compound (331 mg, 78%). 1H NMR (400 MHz, CDCl3): δ 7.94 (s, 1H), 7.29-7.21 (m, 3H), 6.83 (t, 1H), 3.81-3.72 (m, 1H), 3.08-3.01 (m, 2H), 2.81 (t, 2H), 2.36-2.20 (m, 4H), 1.96-1.95 (m, 4H), 1.31 (s, 3H), 1.30 (s, 3H). MS (ESI) m/z: Calculated: 424.5; Observed: 425.1 (M++1).

Workup

  1. extractionextracted with DCM (2×25 mL)
  2. washThe organic layer was washed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customPurification by silica chromatography (2% MeOH-DCM)

Sources & evidence

ORD record
ord-7ee5690d3e0840829fa9be7291d4d34a
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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