Triethylamine → HCID 79633335, compound

HRID 1040797Notes

Reaction equation

HRID 1040797 reaction equation
[CH3:1][C:2]([NH2:6])([CH3:5])[CH2:3][NH2:4].[Cl:7][C:8]1[N:13]=[C:12](Cl)[C:11]([Cl:15])=[CH:10][N:9]=1.CCN(CC)CC.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>C1COCC1>[Cl:7][C:8]1[N:13]=[C:12]([NH:4][CH2:3][C:2]([NH:6][S:23]([CH3:26])(=[O:25])=[O:24])([CH3:5])[CH3:1])[C:11]([Cl:15])=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 31297Methanesulfonyl chlorideHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 79633335HCID 79633335, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-propane-1,2-diamine (2.38 g, 27.03 mmol, 2.83 mL, 1.5 eq.) in THF (100 mL) was cooled to 0 C and 2,4,5-trichloropyrimidine (3.30 g, 18.02 mmol, 2.06 mL, 1.0 eq.) was added. The reaction was stirred for 5 minutes before NEt3 (6.5 mL) and mesyl chloride (3.08 g, 27.03 mmol, 2.08 mL, 1.5 eq.) were added simultaneously via two syringes. After 5 minutes, external cooling was removed and the reaction was stirred under a nitrogen atmosphere for 45 minutes. The reaction was then partitioned between CH2Cl2 (100 mL) and sat. NaHCO3 (100 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (50 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated under reduced pressure onto basic alumina. Purification by basic alumina chromatography (dry loaded) using a gradient of 0-50% EtOAc/hex as the eluting solvent to obtain N-[2-(2,5-dichloro-pyrimidin-4-ylamino)-1,1-dimethyl-ethyl]-methanesulfonamide as a pale yellow solid (3.60 g, 64%). m.p.=143-145° C.; LCMS (m/e) 313 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 8.06 (s, 1H), 6.43-6.32 (m, 1H), 4.82 (s, 1H), 3.74 (d, 2H, J=6.2 Hz), 3.10 (s, 3H), 1.44 (s, 6H).

Workup

  1. additionwas added
  2. additionwere added simultaneously via two syringes
  3. temperatureexternal cooling
  4. customwas removed
  5. customThe reaction was then partitioned between CH2Cl2 (100 mL) and sat. NaHCO3 (100 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (50 mL)
  8. dry with materialThe combined organic layers were dried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure onto basic alumina
  11. customPurification
  12. customby basic alumina chromatography (dry loaded)

Sources & evidence

ORD record
ord-2a00cf6e69a1418cad65b070e2ee3de9
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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