Hydrochloric Acid → HCID 69673829, compound

HRID 2041875Notes

Reaction equation

HRID 2041875 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.O.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 23662686HCID 23662686, compoundHCID 69673660HCID 69673660, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 69673829HCID 69673829, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

200 mg of 4-[2-ethoxycarbonyl-4-phenyl-3-butynylamino]quinazoline and 1 ml of a 1 M tetrahydrofuran solution of lithium dimethylamino borohydride were added to 10 ml of tetrahydrofuran, and the obtained mixture was then stirred at a room temperature for 1 hour. Thereafter, 20 ml of 1 N hydrochloric acid was added to the reaction solution, and the obtained mixture was then stirred for 10 minutes. Thereafter, sodium bicarbonate water was added to the reaction solution for neutralization. The obtained solution was extracted with 40 ml of ethyl acetate twice, and it was then dried over sodium sulfate. The sodium sulfate was filtrated, and the organic layer was then concentrated. The residue was then purified by flash chromatography (manufactured by Biotage AB; Isolera™), so as to obtain 37 mg of 4-[2-hydroxymethyl-4-phenyl-3-butynylamino]quinazoline.

Workup

  1. stirringthe obtained mixture was then stirred for 10 minutes
  2. extractionThe obtained solution was extracted with 40 ml of ethyl acetate twice
  3. dry with materialit was then dried over sodium sulfate
  4. filtrationThe sodium sulfate was filtrated
  5. concentrationthe organic layer was then concentrated
  6. customThe residue was then purified by flash chromatography (manufactured by Biotage AB; Isolera™)

Sources & evidence

ORD record
ord-5ae04c24ea2847e0bf4877958b476b8b
Source dataset
uspto-grants-2013_11
Patent number
US08586505B2

Reaction notes

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