Diisopropylethylamine → HCID 57612673, compound

HRID 2074157Notes

Reaction equation

HRID 2074157 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-3d4c89897d3c46fe85cb12ea8e404173
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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