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Tetrahydro-4H-pyran-4-one → 4-(6-((2H-pyran-4(3H,5H,6H)-ylidene)methyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine

HRID 2091912
Notes
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Reaction equation

HRID 2091912 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[N:11]=[C:10]([CH2:12]P(=O)(OC)OC)[CH:9]=[CH:8][C:6]=2[N:7]=1.C([N-]C(C)C)(C)C.[Li+].[O:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1>C1COCC1>[O:33]1[CH2:38][CH2:37][C:36](=[CH:12][C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)[C:5]=3[N:11]=2)[CH2:35][CH2:34]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 2724682Lithium diisopropylamideHCID 58405032Dimethyl (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylphosphonate

Product 1

HCID 584050234-(6-((2H-pyran-4(3H,5H,6H)-ylidene)methyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Procedure

To a suspension of dimethyl (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylphosphonate from Example 117 (0.45 g) in anhydrous THF (6 mL) at 0° C. was added 2.0 M of lithium diisopropylamide in tetrahydrofuran (1.5 eq). The resulting solution was allowed to warm to RT before adding a solution of dihydro-2H-pyran-4(3H)-one (1.5 eq) in anhydrous THF (3 mL). The reaction mixture was stirred at room temperature for 1 h, then partitioned between brine and Ethyl Acetate. The organic layer was isolated, dried (MgSO4), concentrated and recrystallized from methanol. The light yellow solid was filtered and collected to give 0.36 g of 4-(6-((2H-pyran-4(3H,5H,6H)-ylidene)methyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine as a light yellow solid.

Workup

  1. custompartitioned between brine and Ethyl Acetate
  2. customThe organic layer was isolated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customrecrystallized from methanol
  6. filtrationThe light yellow solid was filtered
  7. customcollected

Sources & evidence

ORD record
ord-c47b8d86f4aa4313923079b222b2eb41
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440651B2

Reaction notes

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