Acetic Acid → HCID 11291450, compound

HRID 898132Notes

Reaction equation

HRID 898132 reaction equation
[CH2:1]([S:7][C:8]1[N:13]=[C:12]([CH:14]=O)[CH:11]=[C:10]([C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(O)(=O)C>C(O)C>[CH2:1]([S:7][C:8]1[N:13]=[C:12]([CH2:14][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:11]=[C:10]([C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8083MorpholineHCID 86067340HCID 86067340, compound

Product 1

HCID 11291450HCID 11291450, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hexylsulfanyl-6-trifluoromethyl-pyrimidine-4-carbaldehyde (0.5 g, 1.7 mmol) and morpholine (0.16 mL, 1.9 mmol) were dissolved in ethanol (5 mL) and acetic acid (0.5 mL) and treated with borane-pyridine complex (0.19 mL, 1.9 mmol) for 4 h at 20° C. The reaction mixture was evaporated to dryness. Extraction: 2×AcOEt, 1×10% aqueous Na2CO3. One obtained a mixture of the expected product and the reduced aldehyde which was more polar. This mixture was separated by chromatography on Si-amine from Silicycle with a gradient of heptane/ethyl acetate from 10:1 up to 1:1. Gave 220 mg (35%) of a colorless oil. MS: m/z=364 (M+H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionExtraction
  3. customOne obtained

Sources & evidence

ORD record
ord-e1a8c220ac084cc4912d4100b0341cd9
Source dataset
uspto-grants-2008_04
Patent number
US07351700B2

Reaction notes

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