Water → HCID 18008044, compound

HRID 2117223Notes

Reaction equation

HRID 2117223 reaction equation
O[CH2:2][CH2:3][CH2:4][N:5]([CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1)[C:6](=[O:8])[CH3:7].[H-].[Na+].Br[CH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[C:25]=1[C:26]([O:28][CH3:29])=[O:27].O.CN1[C:42](=[O:43])N(C)CCC1>C1COCC1>[C:6]([N:5]([CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1)[CH2:4][CH2:3][CH2:2][CH2:42][O:43][CH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[C:25]=1[C:26]([O:28][CH3:29])=[O:27])(=[O:8])[CH3:7]

Participants

7

Reactant 5

HCID 962WaterHCID 24758Sodium hydrideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 10263795Methyl 2-(bromomethyl)-6-methylbenzoateHCID 18008043HCID 18008043, compound

Product 1

HCID 18008044HCID 18008044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-(3-Hydroxy-propyl)-N-quinolin-2-ylmethyl-acetamide (410 mg, 1.5 mmol, EXAMPLE 39a) is dissolved in 20% DMPU in THF (3 mL) and cooled to 0° C. Sodium hydride (60%, 66 mg, 1.65 mmol) is added and the contents are stirred for 10 min. Methyl 2-bromomethyl-6-methyl-benzoate (77%, 365 mg, 1.5 mmol, EXAMPLE 2a) is added. The contents are allowed to come to r.t., and are stirred overnight. The contents are poured into water (100 mL) and extracted with ethyl acetate (3×75 mL). The organic fractions are pooled and washed with water (2×100 mL) and brine (2×100 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) 435 (M+H)+.

Workup

  1. customto come to r.t.
  2. stirringare stirred overnight
  3. extractionextracted with ethyl acetate (3×75 mL)
  4. washwashed with water (2×100 mL) and brine (2×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe crude material is purified by flash chromatography (silica, 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8b82dcf000764cb79f21cac3a3002116
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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