L-Methionine → Carbonimidodithioic acid, N-[6-(2-pyrazinyl)-4-pyrimidinyl]-, dimethyl ester

HRID 1876012Notes

Reaction equation

HRID 1876012 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=1.[OH-].[Na+].[C:16](=S)=[S:17].N[C@H](C(O)=O)C[CH2:22][S:23][CH3:24]>CN(C=O)C.O>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[N:12]=[CH:11][N:10]=[C:9]([N:13]=[C:22]([S:17][CH3:16])[S:23][CH3:24])[CH:8]=1

Participants

7

Reactant 4

HCID 6137L-MethionineHCID 6348Carbon DisulfideHCID 14798Sodium Hydroxide2×HCID 59286556HCID 59286556, compound

Product 1

HCID 59286702Carbonimidodithioic acid, N-[6-(2-pyrazinyl)-4-pyrimidinyl]-, dimethyl esterYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(pyrazin-2-yl)pyrimidin-4-amine (0.2 g, 1.155 mmol) in DMF was added NaOH (0.115 mL, 2.310 mmol), CS2 (0.174 mL, 2.89 mmol), NaOH (0.115 mL, 2.310 mmol) and Met (0.181 mL, 2.89 mmol) at 15 min intervals. Stirring was continued for 1.5 h and the mixture was poured into water. The orange solid was separated, washed with water, dried to give a bright yellow solid (0.14 g, 0.505 mmol, 44%). MS (LC/MS) R.T.=3.19; [M+H]+=278.19.

Workup

  1. customThe orange solid was separated
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-9f277dc66eb848d6b1ef1c046f716566
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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