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Phosphorus oxide (P4O10) → HCID 59803672, compound

HRID 1666223
Notes
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Reaction equation

HRID 1666223 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH3:9])[C:6](=[O:10])[N:5]([CH2:11][C:12]#[CH:13])[C:4](=[O:14])[C:3]=1[NH:15][C:16](=O)[C:17]#[C:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>CN(C)C=O>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:18]#[C:17][C:16]2[NH:15][C:3]3[C:4](=[O:14])[N:5]([CH2:11][C:12]#[CH:13])[C:6](=[O:10])[N:7]([CH2:8][CH3:9])[C:2]=3[N:1]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 598036863-(3,4-Dimethoxyphenyl)propynoic acid (6-amino-1-ethyl-3-prop-2-ynyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)amide

Product 1

HCID 59803672HCID 59803672, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(3,4-dimethoxyphenyl)propynoic acid (6-amino-1-ethyl-3-prop-2-ynyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)amide (3.2 g, 8.0 mmol) in 15 ml of dry dimethylformamide was added phosphorous pentoxide (6 g). The mixture was stirred at 100° C. for 10 min and subsequently cooled to room temperature. The product was precipitated by adding water (ca. 100 ml), filtered under reduced pressure, washed thoroughly with water and dried at 70° C., yielding light yellow 8-(3,4-dimethoxyphenylethynyl)-3-ethyl-1-prop-2-ynyl-3,7-dihydro-purine-2,6-dione (2.5 g, 82%).

Workup

  1. temperaturesubsequently cooled to room temperature
  2. customThe product was precipitated
  3. additionby adding water (ca. 100 ml)
  4. filtrationfiltered under reduced pressure
  5. washwashed thoroughly with water
  6. customdried at 70° C.

Sources & evidence

ORD record
ord-4a30e4eef2674f88aa45d9bd6a79583c
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044061B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes