3,4-dihydro-2H-pyran → 4-(5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

HRID 500710Notes

Reaction equation

HRID 500710 reaction equation
[I:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=1.[CH2:15]1[CH2:20][O:19][CH:18]=[CH:17][CH2:16]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>>[I:1][C:2]1[N:6]([CH:18]2[CH2:17][CH2:16][CH2:15][CH2:20][O:19]2)[N:5]=[CH:4][C:3]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=1

Participants

4

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 468641604-(5-Iodo-1H-pyrazol-4-yl)-2-(methylsulfanyl)pyrimidine

Product 1

HCID 578563134-(5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidineYield 60,933.301%

Conditions

Temperature
60 °C

Procedure

A mixture of compound A (75.0 g, 0.235 mmol), DHP (39.6 g, 0.471 mmol) and TsOH.H2O (7.5 g) was stirred at 60° C. for 6 h. The mixture was cooled to room temperature and concentrated. The residue was purified by chromatography (EtOAc:petroleum ether=1:15) to give 4-(5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine (B) (57.6 g, 60.8%). 1H NMR (400 MHz, CDCl3): δ 8.495 (d, 1H), 8.400 (s, 1H), 7.638 (d, 1H), 5.398 (m, 1H), 4.070 (m, 1H), 3.732 (m, 1H), 2.796 (s, 3H), 2.110 (m, 3H), 1.900 (m, 3H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography (EtOAc:petroleum ether=1:15)

Sources & evidence

ORD record
ord-dacbebed5a51416781b0f6dd9ba4a5bb
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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