2-Amino-4,6-dimethyl pyrimidine → HCID 86738107, compound

HRID 1155339Notes

Reaction equation

HRID 1155339 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.C([Li])CCC.[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([N:25]=[C:26](Cl)[O:27][CH3:28])(=[O:24])=[O:23]>O1CCCC1.CCCCCC>[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([N:25]=[C:26]([O:27][CH3:28])[NH:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 53650123HCID 53650123, compoundHCID 178418339Butyllithium

Product 1

HCID 86738107HCID 86738107, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To 1.2 g of 2-amino-4,6-dimethylpyrimidine in 50 ml of tetrahydrofuran is added 6.85 ml of 1.6 molar n-butyl lithium in hexane at 0°. The mixture is stirred for 15 minutes. To this solution is added dropwise, a solution of 2.1 g of methyl N-(2-methylphenylsulfonyl)carbonimidochloridate in 5 ml of tetrahydrofuran at 0°-10°. This reaction mixture is stirred for 30 minutes at 0°-10° and 30 minutes at ambient temperature. The reaction mixture is filtered and the solvent is stripped from the filtrate under reduced pressure to yield a crude product. The crude product is further purified via dry column chromatography on silica gel with ethyl acetate as the eluent. Pure N'-(2-methylphenylsulfonyl)-N-(4,6-dimethylpyrimidin-2-yl)carbamimidic acid, methyl ester is obtained.

Workup

  1. additionTo this solution is added dropwise
  2. customat 0°-10°
  3. stirringThis reaction mixture is stirred for 30 minutes at 0°-10° and 30 minutes at ambient temperature
  4. filtrationThe reaction mixture is filtered
  5. customto yield a crude product
  6. customThe crude product is further purified
  7. dry with materialvia dry column chromatography on silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-0b6ddc93bd6a4af4901319b14a09aaa1
Source dataset
uspto-grants-1981_11
Patent number
US04301286

Reaction notes

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