Acetic Acid → HCID 86713577, compound

HRID 524053Notes

Reaction equation

HRID 524053 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([CH:9]=O)=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[NH2:18].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH3:23][O:22][C:20]1[CH:19]=[C:17]([NH:18][CH2:9][C:8]2[C:3]([NH:2][CH3:1])=[N:4][C:5]([S:11][CH3:12])=[N:6][CH:7]=2)[CH:16]=[C:15]([O:14][CH3:13])[CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 663013,5-DimethoxyanilineHCID 5003444Sodium cyanoborohydrideHCID 106075204-(Methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

Product 1

HCID 86713577HCID 86713577, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde (1.0 g, 5.46 mmol) and 3,5-dimethoxyaniline (840 mg, 5.46 mmol) in methanol (60 mL) was stirred at RT for 3 h, followed by the addition of sodium cyanoborohydride (520 mg, 8.20 mmol) and 1 mL of acetic acid. The reaction mixture was then stirred at RT for another 4 h. LCMS showed the reaction was completed. The reaction was quenched by 30 mL of 1N HCl, then stirred for 0.5 h and extracted with ethyl acetate (3×50 mL). The organic layers were separated, combined, washed with saturated aqueous solution of sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated to afford the title compound (crude 1.2 g, 69%) as a white solid, which was directly used in the next step without further purification. MS (ES+) C15H20N4O2S requires: 320. found: 321 [M+H]+.

Workup

  1. stirringThe reaction mixture was then stirred at RT for another 4 h
  2. customThe reaction was quenched by 30 mL of 1N HCl
  3. stirringstirred for 0.5 h
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. customThe organic layers were separated
  6. washwashed with saturated aqueous solution of sodium bicarbonate and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-be11da021ead4205b1520d69d2adbe8f
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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