2-(Dimethylamino)ethanol → HCID 25060731, compound

HRID 2244057Notes

Reaction equation

HRID 2244057 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[NH2:9][C:10]1[C:19]2[C:14](=[C:15](F)[C:16]([N:20]3[C:28]4[CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][C:24](=[O:31])[C:23]=4[C:22]([CH3:32])=[CH:21]3)=[CH:17][CH:18]=2)[N:13]=[CH:12][N:11]=1>CN(C=O)C>[NH2:9][C:10]1[C:19]2[C:14](=[C:15]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[C:16]([N:20]3[C:28]4[CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][C:24](=[O:31])[C:23]=4[C:22]([CH3:32])=[CH:21]3)=[CH:17][CH:18]=2)[N:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 25060729HCID 25060729, compound

Product 1

HCID 25060731HCID 25060731, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a microwave vial with a stir bar, N,N-dimethylethanolamine (101 mg, 1.13 mmol) is dissolved in DMF (5 mL). To this solution is added sodium hydride (60% suspension in mineral oil, 45 mg, 1.136 mmol) and the mixture stirred at room temperature for 5 minutes and 1-(4-Amino-8-fluoro-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one (192 mg, 0.568 mmol) is added. The reaction is sealed and placed in the microwave reactor where it is heated to 150° C. for 30 minutes. The reaction is cooled, quenched by adding 25 mL sat. NH4Cl (aq) and extracted with CH2Cl2 (3×5 mL). The combined organics are dried with Na2SO4, concentrated and purified by silica gel chromatography by two gradient runs on the same column, the first 0% to 100% ethyl acetate in hexanes and the second 0% to 50% methanol in ethyl acetate. This gives 1-[4-Amino-8-(2-dimethylamino-ethoxy)-quinazolin-7-yl]-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one as a yellow powder (171 mg, 74% yield) (LC/MS m/z=408 [M+H]+).

Workup

  1. customThe reaction is sealed
  2. temperatureis heated to 150° C. for 30 minutes
  3. temperatureThe reaction is cooled
  4. customquenched
  5. additionby adding 25 mL sat. NH4Cl (aq)
  6. extractionextracted with CH2Cl2 (3×5 mL)
  7. dry with materialThe combined organics are dried with Na2SO4
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography by two gradient runs on the same column

Sources & evidence

ORD record
ord-666c4c42bf52464a85f2f7ba4c0f1972
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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