Dimethyl Sulfide → HCID 21912368, compound

HRID 2307993Notes

Reaction equation

HRID 2307993 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[C:12]([C:13](O)=[O:14])=[C:11]([NH:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[N:10]=[C:9]([CH3:26])[N:8]=1)[CH2:4][CH3:5])[CH3:2].CSC>C1COCC1>[CH2:1]([CH:3]([O:6][C:7]1[C:12]([CH2:13][OH:14])=[C:11]([NH:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[N:10]=[C:9]([CH3:26])[N:8]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 21912243HCID 21912243, compound

Product 1

HCID 21912368HCID 21912368, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-ethyl-propoxy)-2-methyl-6-(2,4,6-trimethyl-phenylamino)-pyrimidine-5-carboxylic acid in dry THF was added BH3.DMS. The resulting mixture was heated at reflux. The mixture was quenched with dilute HCl and stirred for 30 minutes;, adjusted pH to 7.5-8.5, then extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give a crude material. The crude material was purified through silica gel column chromatography to give the title compound as a solid, mp. 121-123° C., Anal. For C20H29N3O2 calc. C, 69.94; H, 8.51; N, 12.23; found: C, 69.73; H, 8.47; N, 11.99.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux
  3. customThe mixture was quenched with dilute HCl
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customto give a crude material
  9. customThe crude material was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-69d4f8b4793045a295d12b7810456332
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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