Sodium Hydroxide → HCID 10951346, compound

HRID 1598540Notes

Reaction equation

HRID 1598540 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:18]=[C:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH2:5][CH2:4]1.Cl[C:25]1([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])[N:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26]1.CCN(C(C)C)C(C)C.[OH-].[Na+]>C(#N)CCC.C(OCC)(=O)C>[CH2:38]([N:35]([CH2:36][CH3:37])[C:25]1[N:34]=[C:33]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]3[N:18]=[C:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=3)[CH2:5][CH2:4]2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1)[CH3:39]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 11001505HCID 11001505, compoundHCID 18929549HCID 18929549, compound

Product 1

HCID 10951346HCID 10951346, compound

Reagents, catalysts & solvents 2

HCID 8008ButyronitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound of Example III (500 mg, 1.8 mmol), 2-chloro-2-diethylaminoquinazoline (467 mg, 2.0 mmol) and Hunig's base (0.4 ml), 2.7 mmol) in 5 ml of butyronitrile was reacted for 12 hours at 120° C. After cooling, ethyl acetate (50 ml) and 50 ml of sodium hydroxide (10%) were added. The phases were separated and the aqueous phase was extracted with ethyl acetate (2×25 ml). The combined organic phases were dried (Na2SO4), concentrated on a rotary evaporator and purified by chromatography on silica gel (eluent: methylene chloride/ethanol/ammonia, 100/10/1) to give the free base as a solid.

Workup

  1. customwas reacted for 12 hours at 120° C
  2. temperatureAfter cooling
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (2×25 ml)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated on a rotary evaporator
  7. custompurified by chromatography on silica gel (eluent: methylene chloride/ethanol/ammonia, 100/10/1)

Sources & evidence

ORD record
ord-263ce1f59a2f46b89547f94de29e8b3a
Source dataset
uspto-grants-1998_04
Patent number
US05739127

Reaction notes

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