Propargyl alcohol → HCID 178522931, compound

HRID 1581560Notes

Reaction equation

HRID 1581560 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]2[N:11]=[CH:10][C:9]([C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[O:13])=[C:8]([OH:23])[C:6]=2[N:7]=1.C(N(CC)CC)C.[CH2:31]([OH:34])[C:32]#[CH:33].[NH4+].[Cl-]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:12]([C:9]2[CH:10]=[N:11][C:5]3[CH:4]=[N:3][C:2]([C:33]#[C:32][CH2:31][OH:34])=[N:7][C:6]=3[C:8]=2[OH:23])=[O:13])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 178522930HCID 178522930, compound

Product 1

HCID 178522931HCID 178522931, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-bromo-N-(4-chlorobenzyl)-8-hydroxypyrido[3,2-d]pyrimidine-7-carboxamide (Preparation 6, 1.97 g), (Ph3P)2PdCl2 (175 mg), and triethylamine (5.0 mL) in DMF (50 mL) is heated to 90° C. Propargyl alcohol (2.5 mL) is slowly added to the mixture over 20 h. The reaction mixture is allowed to cool to room temperature, poured into saturated aqueous NH4Cl solution (200 mL), and extracted with ethyl acetate (3×100 mL). The combined organic layers are dried (MgSO4) and concentrated. The crude product is purified by column chromatography.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-210fc15bc064469f880c4796cf18c38c
Source dataset
uspto-grants-2004_05
Patent number
US06730682B2

Reaction notes

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