Triethylamine → 4-Cyclopropyl-6-diethoxymethyl-2-hexylsulfanyl-pyrimidine

HRID 898126Notes

Reaction equation

HRID 898126 reaction equation
[CH:1]1([C:4](=O)[C:5]#[C:6][CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])[CH2:3][CH2:2]1.Br.[CH2:16]([S:22][C:23](=[NH:25])[NH2:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(N(CC)CC)C>C1COCC1>[CH:1]1([C:4]2[CH:5]=[C:6]([CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])[N:25]=[C:23]([S:22][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[N:24]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12387367(Hexylsulfanyl)methanimidamide hydrobromideHCID 692932841-Cyclopropyl-4,4-diethoxy-2-butyn-1-one

Product 1

HCID 692920874-Cyclopropyl-6-diethoxymethyl-2-hexylsulfanyl-pyrimidineYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Cyclopropyl-4,4-diethoxy-but-2-yn-1-one (2 g, 10 mmol) and 2-hexyl-isothiourea hydrobromide (2.7 g, 11.2 mmol) were dissolved under nitrogen in THF (20 mL). Then triethylamine (3.1 mL, 22.4 mmol) was added slowly. The reaction was slightly exothermic (28° C.). The suspension was stirred for 5 h at 20° C. The product was extracted with AcOEt, sat. NH4Cl solution, dried and concentrated. The residue was purified by silica gel chromatography in heptane/ethyl acetate 95:5. One obtained 2.86 g (83%) of a colorless oil. MS: m/z=339 (M+H).

Workup

  1. custom(28° C.)
  2. extractionThe product was extracted with AcOEt, sat. NH4Cl solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography in heptane/ethyl acetate 95:5

Sources & evidence

ORD record
ord-33d86b629e474bcd94b0e9c3e82a1394
Source dataset
uspto-grants-2008_04
Patent number
US07351700B2

Reaction notes

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