Acetic Acid → HCID 86677570, compound

HRID 2401113Notes

Reaction equation

HRID 2401113 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:11][CH:12]=O)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].Cl[CH:15](Cl)C.[Cl:18][C:19]1[N:24]=[CH:23][C:22]([NH2:25])=[CH:21][N:20]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH2:6][CH2:15][NH:25][C:22]1[CH:21]=[N:20][C:19]([Cl:18])=[N:24][CH:23]=1)([CH2:11][CH3:12])[CH2:10][CH2:9][O:8][CH3:7]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 122159932-Chloropyrimidin-5-amineHCID 58468045methyl 4-(2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate

Product 1

HCID 86677570HCID 86677570, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-oxo-ethyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (0.12 g, 0.644 mmol) in 1-2 dichloroethane (DCE, 6 mL) was added 2-chloropyrimidin-5-amine (0.084 g, 0.644 mmol), acetic acid (3.1 eq) and allowed to stir at room temperature for an hour. NaBH(OAc)3 (3 eq) was then added in one portion and reaction mixture allowed to stir at room temperature for 16 hours. The reaction was diluted with DCM (10 mL), quenched with 2 M of NH4OH in water (1 mL). The layers were separated, and the aqueous layer was extracted with DCM (10 mL, 2×). The combined organic layers were washed with aqueous NaHCO3 (10 mL), brine (20 mL), dried over Na2SO4, and concentrated under vacuum. Purification over silica gel eluting with ethyl acetate in heptanes (0-75%) afforded 0.088 g (46%) of title compound.

Workup

  1. stirringto stir at room temperature for 16 hours
  2. customquenched with 2 M of NH4OH in water (1 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (10 mL, 2×)
  5. washThe combined organic layers were washed with aqueous NaHCO3 (10 mL), brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customPurification over silica gel eluting with ethyl acetate in heptanes (0-75%)

Sources & evidence

ORD record
ord-d7f8ed89da6442228f50696586182516
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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