Ethylenediamine → HCID 79632714, compound

HRID 1040787Notes

Reaction equation

HRID 1040787 reaction equation
[CH2:1]([NH2:4])[CH2:2]N.[Cl:5][C:6]1[N:11]=[C:10](Cl)[C:9]([Cl:13])=[CH:8][N:7]=1.CC[N:16](CC)CC.[S:21](Cl)([CH3:24])(=[O:23])=[O:22]>C1COCC1>[Cl:5][C:6]1[N:11]=[C:10]([NH:4][CH2:1][CH2:2][CH2:24][S:21]([NH2:16])(=[O:23])=[O:22])[C:9]([Cl:13])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 79632714HCID 79632714, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethylene diamine (2.99 g, 49.8 mmol, 2.05 mL, 1.5 eq.) in THF (200 mL) was cooled to 0° C. and 2,4,5-trichloropyrimidine (6.08 g, 33.2 mmol, 3.80 mL, 1.0 eq.) was added. A precipitate formed and the reaction was stirred for 5 minutes before NEt3 and mesyl chloride 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 (150 mL) and sat. NaHCO3 (150 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (100 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated under reduced pressure onto silica gel. Purification by silica gel chromatography (dry loaded) using a gradient of 0-100% EtOAc/hex followed by 0-20% MeOH/EtOAc as the eluting solvent to obtain -[2-(2,5-dichloro-pyrimidin-4-ylamino)-ethyl]-methanesulfonamide as a white solid (763 mg, 8%). m.p.=186-187° C.; LCMS (m/e) 285 (M+1); 1H-NMR (d6-DMSO, 400 MHz) δ 8.18 (s, 1H), 7.92 (t, 1H, J=5.3 Hz), 7.17 (t, 1H, J=5.7 Hz), 3.49 (dt, 2H, J=6.1 and 6.2 Hz), 3.16 (dt, 2H, J=6.2 and 6.3 Hz), 2.92 (s, 3H).

Workup

  1. customA precipitate formed
  2. additionwere added simultaneously via two syringes
  3. temperatureexternal cooling
  4. customwas removed
  5. customThe reaction was then partitioned between CH2Cl2 (150 mL) and sat. NaHCO3 (150 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (100 mL)
  8. dry with materialThe combined organic layers were dried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure onto silica gel
  11. customPurification
  12. customby silica gel chromatography (dry loaded)

Sources & evidence

ORD record
ord-0bd69c452b4d4ab39dd398913db18dcc
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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