Water → HCID 18008082, compound

HRID 2117226Notes

Reaction equation

HRID 2117226 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].[H-].[Na+].Br[CH2:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:22]=1[C:23]([O:25][CH3:26])=[O:24].O>CN1C(=O)N(C)CCC1.C1COCC1>[CH3:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][O:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[C:22]=1[C:23]([O:25][CH3:26])=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10263795Methyl 2-(bromomethyl)-6-methylbenzoateHCID 18008060HCID 18008060, compound

Product 1

HCID 18008082HCID 18008082, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
0 °C

Procedure

4-(Quinolin-2-ylamino)-butan-1-ol (432 mg, 2.0 mmol, EXAMPLE 42a) is dissolved in 20% DMPU in THF (5 mL) and cooled to 0° C. Sodium hydride (60%, 88 mg, 2.2 mmol) is added portionwise, and the contents are stirred for 10 min. Methyl 2-bromomethyl-6-methyl-benzoate (77%, 631 mg, 2.0 mmol, EXAMPLE 2a) is added and the contents are allowed to warm to r.t. and continue to stir overnight. The reaction contents are poured into water (100 mL) and extracted with ethyl acetate (3×75 mL). Sodium chloride is added to the aqueous layer on the second and third extractions. The organic fractions are pooled, washed with brine (2×150 mL), dried over MgSO4, filtered and reduced under vacuum to an oil. The crude material is purified by flash chromatography (silica, 3% methanol in dichloromethane) to give the title compound. MS (ESI) 379 (M+H)+.

Workup

  1. temperatureto warm to r.t.
  2. stirringto stir overnight
  3. customThe reaction contents
  4. extractionextracted with ethyl acetate (3×75 mL)
  5. additionSodium chloride is added to the aqueous layer on the second and
  6. extractionthird extractions
  7. washwashed with brine (2×150 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe crude material is purified by flash chromatography (silica, 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-da6b9e627ad44cf88af6d27e73a72e8e
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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