(Diethylamino)sulfur trifluoride → HCID 53339260, compound

HRID 1425602Notes

Reaction equation

HRID 1425602 reaction equation
[N:1]1[C:2]2[N:3]([C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)[CH:4]=[CH:5][C:6]=1[C:7]#[C:8][CH2:9][CH2:10][CH2:11]O.C(N(S(F)(F)[F:26])CC)C>C(Cl)Cl>[F:26][CH2:11][CH2:10][CH2:9][C:8]#[C:7][C:6]1[CH:5]=[CH:4][N:3]2[C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=[C:2]2[N:1]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 58362540HCID 58362540, compound

Product 1

HCID 53339260HCID 53339260, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-(benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)pent-4-yn-1-ol (20 mg, 0.08 mmol) in 1 mL dry DCM at 0° C. was added (Diethylamino)sulfur trifluoride (64 mg, 0.4 mmol) dropwise. The reaction was warmed to rt and stirred for 1 h and quenched onto a mixture of ice (10 g) in saturated Na2CO3 (10 mL). The mixture was extracted with EtOAc (2×10 mL) and the organic phase was dried over MgSO4 and concentrated. The residue was purified by silica chromatography (EtOAc in DCM, 5% to 50%) to afford 2-(5-fluoropent-1-yn-1-yl)benzo[4,5]imidazo[1,2-a]pyrimidine as a yellow oil (3 mg, 15%). 1H NMR (400 MHz, CDCl3): δ 8.65 (d, J=6.8 Hz, 1H), 8.03 (d, J=8 Hz, 1H), 7.85 (d, J=8 Hz, 1H), 7.58 (m, 1H), 7.43 (m, 1H), 6.93 (d, J=7.2 Hz, 1H), 4.69 (t, J=5.6 Hz, 1H), 4.57 (t, J=5.6 Hz, 1H), 2.70 (t, J=5.6 Hz, 2H), 2.14-2.00 (m, 2H); MS (ESI) m/z [M+H]+254.

Workup

  1. customquenched onto a mixture of ice (10 g) in saturated Na2CO3 (10 mL)
  2. extractionThe mixture was extracted with EtOAc (2×10 mL)
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica chromatography (EtOAc in DCM, 5% to 50%)

Sources & evidence

ORD record
ord-5c67588a841e4879809dc94526ab0f71
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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