Hydrochloric Acid → HCID 69673829, compound

HRID 1527617Notes

Reaction equation

HRID 1527617 reaction equation
C([O:3][C:4]([CH:6]([C:19]#[C:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][N:10]=1)=O)C.CN([BH3-])C.[Li+].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:3][CH2:4][CH:6]([C:19]#[C:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23662686HCID 23662686, compoundHCID 69673660HCID 69673660, compound

Product 1

HCID 69673829HCID 69673829, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 10 ml of tetrahydrofuran were added 200 mg of 4-[2-ethoxycarbonyl-4-phenyl-3-butynylamino]quinazoline and 1 ml of a lithium dimethylaminoborohydride solution (1 M in tetrahydrofuran), and the mixture was stirred at room temperature for an hour. To the reaction mixture, 20 ml of 1 N HCl was added and the mixture was stirred for 10 minutes. The reaction mixture was neutralized with an added aqueous solution of sodium hydrogencarbonate; thereafter, two extractions were conducted with 40 ml of ethyl acetate, followed by drying over sodium sulfate. After filtering the sodium sulfate, the organic layer was concentrated and purified by means of flash chromatography (Isolera™ manufactured by Biotage AB) to give 37 mg of 4-[2-hydroxymethyl-4-phenyl-3-butynylamino]quinazoline.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. extractionthereafter, two extractions
  3. dry with materialby drying over sodium sulfate
  4. filtrationAfter filtering the sodium sulfate
  5. concentrationthe organic layer was concentrated
  6. custompurified by means of flash chromatography (Isolera™ manufactured by Biotage AB)

Sources & evidence

ORD record
ord-11bc291d59944fcfa969775bbc6480e6
Source dataset
uspto-grants-2015_07
Patent number
US09089139B2

Reaction notes

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