Tetrahydrofuran → 1100598-15-9

HRID 2042748Notes

Reaction equation

HRID 2042748 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=2)[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)=[N:13]2)=[N:6][CH:7]=1.C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:53][CH2:54][N:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[CH3:24][N:22]1[CH:23]=[C:19]([C:14]2[CH:15]=[CH:16][C:17](=[O:18])[N:12]([CH2:11][C:10]3[CH:25]=[CH:26][CH:27]=[C:8]([C:5]4[N:6]=[CH:7][C:2]([O:1][CH2:53][CH2:54][N:55]5[CH2:60][CH2:59][O:58][CH2:57][CH2:56]5)=[CH:3][N:4]=4)[CH:9]=3)[N:13]=2)[CH:20]=[N:21]1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5363146Diisopropyl azodicarboxylateHCID 59438049HCID 59438049, compound

Product 1

HCID 251346921100598-15-9

Procedure

To a suspension of 360 mg (1.00 mmol) of 2-[3-(5-hydroxy-pyrimidin-2-yl)-benzyl]-6-(1-methyl-1H-pyrazol-4-yl)-2H-pyridazin-3-one in 2 ml THF 394 mg (1.50 mmol) of triphenylphosphine and 242 μl (2.00 mmol) of 4-(2-hydroxyethyl)morpholine are added one after the other. Under ice cooling 294 μl (1.50 mmol) of diisopropylazodicarboxylate are slowly added dropwise. The resulting solution is stirred for 18 hours at room temperature. The reaction mixture is then concentrated in vacuo and the oily residue is dissolved in 2-propanol. The resulting solid of 6-(1-methyl-1H-pyrazol-4-yl)-2-{3-[5-(2-morpholin-4-yl-ethoxy)-pyrimidin-2-yl]-benzyl}-2H-pyridazin-3-one resulted after some time is sucked off, washed with 2-propanol and tert-butylmethylether and dried in vacuo.

Workup

  1. additionare added one after the other
  2. concentrationThe reaction mixture is then concentrated in vacuo
  3. dissolutionthe oily residue is dissolved in 2-propanol

Sources & evidence

ORD record
ord-41542f81f234402a8d820d2b9d6c6382
Source dataset
uspto-grants-2013_11
Patent number
US08586599B2

Reaction notes

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