HCID 59258597, compound → HCID 60057263, compound

HRID 544860Notes

Reaction equation

HRID 544860 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][O:9][C:10]1[N:15]=[C:14]([C:16](OC)=[O:17])[CH:13]=[C:12]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:11]=1.[BH4-].[Na+].C(O)C>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][O:9][C:10]1[N:15]=[C:14]([CH:16]=[O:17])[CH:13]=[C:12]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[N:11]=1

Participants

5

Reactant 2

HCID 59258597HCID 59258597, compoundHCID 131728818HCID 131728818, compound

Product 1

HCID 60057263HCID 60057263, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

Preparation of alcohol derivative used to prepare Compounds 1-4: To a solution of 2-[2-(pyridin-2-yl)-ethoxy]-4-(methoxycarbonyl)-6-(morpholin-4-yl)-pyrimidine (0.81 g, 2.35 mmol) in ethanol sodium borohydride (4 eq, 0.36 g) was added in portions and the reaction mixture was refluxed for 3 hours. Solvent was removed, the reaction mixture distributed between ethyl acetate and water, organic solution washed with brine, dried and concentrated to give crude alcohol. The above alcohol (0.64 g, 2 mmol) was heated in toluene at 85° C. with manganese dioxide, (10 eq, 1.75 g) for 4 hours to give 2-[2-(pyridin-2-yl)-ethoxy]-4-formyl-6-(morpholin-4-yl)-pyrimidine (0.3 g, 48%) which was isolated by column chromatography.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. customSolvent was removed
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give crude alcohol

Sources & evidence

ORD record
ord-c53be2e999934421abc21066e89cc146
Source dataset
uspto-grants-2011_05
Patent number
US07935698B2

Reaction notes

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