Diisopropylethylamine → HCID 57612673, compound

HRID 600406Notes

Reaction equation

HRID 600406 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[C:13]([Cl:15])[C:12]([N+:16]([O-:18])=[O:17])=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[NH2:29][CH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C1COCC1>[CH2:1]([S:8][C:9]1[N:10]=[C:11]([NH:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[C:12]([N+:16]([O-:18])=[O:17])=[C:13]([Cl:15])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 22288487HCID 22288487, compound

Product 1

HCID 57612673HCID 57612673, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(benzylthio)-4,6-dichloro-5-nitropyrimidine (WO 01/58906 A1) (9 g, 28.5 mmol) in THF (60 mL) and DIEA (9.9 mL, 7.36 g, 57 mmol, 2 equiv.) was added drop wise a solution of 4-aminotetrahydropyran (2.77 g, 27.4 mmol, 0.96 equiv.) in THF (20 mL) over 15 min. The reaction mixture was stirred at room temperature for 18 h. The solvent was then removed in vacuo and the residue purified by column chromatography (silica gel, elution with 4/1 hexanes/ethyl acetate) to afford, after evaporation and drying, the desired product as a yellow solid (7.59 g, 70% yield). 1H NMR (300 MHz, CDCl3) δ, ppm: 7.86 (br d, J=6.8 Hz, 1H), 7.42-7.36 (m, 2H), 7.36-7.27 (m, 3H), 4.38 (s, 2H), 4.31-4.20 (m, 1H), 3.96 (dt, J=11.7, 3.5 Hz, 2H), 3.47 (ddd, J=11.7, 11.3, 2.2 Hz, 2H), 1.92 (br dd, J=12.4, 2.2 Hz, 2H), 1.66-1.52 (m, 2H).

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue purified by column chromatography (silica gel, elution with 4/1 hexanes/ethyl acetate)
  3. customto afford
  4. customafter evaporation
  5. customdrying

Sources & evidence

ORD record
ord-39b07608f5ac47ac85ebc566a5851230
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

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