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Morpholine → 2-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

HRID 645513
Notes
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Reaction equation

HRID 645513 reaction equation
C([O:4][C:5]([C:7]1[C:8]([O:15][CH2:16][CH:17]2[CH2:24][CH2:23][C:20]3([CH2:22][CH2:21]3)[CH2:19][CH2:18]2)=[N:9][C:10]([C:13]#[N:14])=[N:11][CH:12]=1)=[O:6])C=C.N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]([C:10]1[N:9]=[C:8]([O:15][CH2:16][CH:17]2[CH2:24][CH2:23][C:20]3([CH2:22][CH2:21]3)[CH2:19][CH2:18]2)[C:7]([C:5]([OH:6])=[O:4])=[CH:12][N:11]=1)#[N:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8083MorpholineHCID 687066042-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

Product 1

HCID 687069622-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of a 2-cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester (0.096 mmol) in THF (1.0 mL) are added Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium) (0.0096 mmol) and morpholine (0.19 mmol) at room temperature. The reaction mixture is stirred at room temperature for 0.5 h and the reaction is quenched by the addition of sat. aq. NaHCO3. The mixture is extracted with ether. The aqueous layer is acidified to pH 2 with sat. aq. KHSO4. The mixture is extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude titled compound.

Workup

  1. customthe reaction is quenched by the addition of sat. aq. NaHCO3
  2. extractionThe mixture is extracted with ether
  3. extractionThe mixture is extracted with AcOEt
  4. washThe organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1360f99a564e4119b2fce54cea85024d
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07704996B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes