Triethylamine → 2-(Methylsulfonyl)pyrimidin-4-amine

HRID 1678221Notes

Reaction equation

HRID 1678221 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8]([CH3:11])(=[O:10])=[O:9])[N:3]=1.S1C(C2C=C(N)C=C3C=2N[N:23]=C3)=CC2C=CC=CC1=2.CCN(CC)CC>COCCOC>[CH3:11][S:8]([C:4]1[N:3]=[C:2]([NH2:23])[CH:7]=[CH:6][N:5]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111482324-Chloro-2-(methylsulfonyl)pyrimidineHCID 59023728HCID 59023728, compound

Product 1

HCID 183768662-(Methylsulfonyl)pyrimidin-4-amineYield 85.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a mixture of 4-chloro-2-methanesulfonyl-pyrimidine (2.54 g, 13.2 mmol) in DME (20 mL) was added a mixture of 7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamine (Example #F.8.1, 1.95 g, 7.35 mmol) and Et3N (1.43 mL, 10.3 mmol) in DME (160 mL). The reaction mixture was stirred at room temperature for about 16 hours then filtered, then filtrate was adsorbed onto alumina. The mixture was purified by flash column chromatography over alumina using CH2Cl2/MeOH (99:1) as an eluent to yield the initial crop of product. A second crop was obtained by triturating the alumina in CH2Cl2/MeOH (8:2) and combined with the first to afford 7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-(2-methanesulfonyl-pyrimidin-4-yl)-amine (1.09 g, 36% yield): LC/MS (method e) Rt 1.8 min; m/z (ESI−): (M−H)+ 419.9.

Workup

  1. additionwas added
  2. filtrationthen filtered
  3. customThe mixture was purified by flash column chromatography over alumina
  4. customto yield the initial crop of product
  5. customA second crop was obtained
  6. customby triturating the alumina in CH2Cl2/MeOH (8:2)

Sources & evidence

ORD record
ord-5a1152be1c14494aa38182f71b6e7ed2
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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