Dimethyl Sulfoxide → HCID 63282366, compound

HRID 2174214Notes

Reaction equation

HRID 2174214 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Cl.[NH:12]1[CH2:15][CH:14]([OH:16])[CH2:13]1.CCN(C(C)C)C(C)C.CS(C)=O>O.C(#N)C>[N+:8]([C:5]1[CH:4]=[N:3][C:2]([N:12]2[CH2:15][CH:14]([OH:16])[CH2:13]2)=[N:7][CH:6]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 825442-Chloro-5-nitropyrimidineHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 63282366HCID 63282366, compoundYield 105.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-chloro-5-nitro-pyrimidine (100 mg, 0.63 mmol), azetidin-3-ol hydrochloride (137 mg, 1.25 mmol), DIPEA (0.44 mL, 2.51 mmol) and DMSO (2 mL) were combined and stirred at it for 1 hr. The reaction mixture was partitioned with brine (50 mL) and THF (50 mL). The organic (THF) layer was separated, and the aqueous layer was extracted with a further portion of THF (50 mL). The organic fractions were combined, dried (MgSO4) and concentrated in vacuo to give an oil. The oil was taken up in a mixture of water and acetonitrile and freeze-dried to give (i) as a light yellow solid (130 mg). 1H NMR (400 MHz, Acetone) δ 9.03 (s, 2H), 4.91-4.64 (m, 1H), 4.49 (ddd, J=10.5, 6.6, 1.7 Hz, 2H), 4.04 (ddd, J=10.4, 4.3, 1.7 Hz, 2H).

Workup

  1. customThe reaction mixture was partitioned with brine (50 mL) and THF (50 mL)
  2. customThe organic (THF) layer was separated
  3. extractionthe aqueous layer was extracted with a further portion of THF (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customfreeze-dried

Sources & evidence

ORD record
ord-af70bc0979084b9d90aff647a597adab
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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