Sodium hydride → HCID 18381603, compound

HRID 2268907Notes

Reaction equation

HRID 2268907 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12]([C:21]#[C:22]C(C)(O)C)=[N:11][N:10]=1.[H-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12]([C:21]#[CH:22])=[N:11][N:10]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18381655HCID 18381655, compound

Product 1

HCID 18381603HCID 18381603, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a Claisen flask, a suspension under N2 of 4-[4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-phthalazin-1-yl]-2-methyl-but-3-yn-2-ol (0.4 g, 1 mmole), prepared as described in example 107, in dry toluene (50 ml) was added with a catalytic amount of NaH, the mixture was refluxed, then distilled up to half volume. The mixture was left to stand overnight, then poured into water, extracted three times with CH2Cl2, discoloured with charcoal, filtered over celite and dried to give a solid which was triturated in ethyl ether to give 0.21 g of the title compound. m.p.: 210.3-211.3° C. (dec.).

Workup

  1. temperaturethe mixture was refluxed
  2. distillationdistilled up to half volume
  3. waitThe mixture was left
  4. additionpoured into water
  5. extractionextracted three times with CH2Cl2
  6. filtrationfiltered over celite
  7. customdried
  8. customto give a solid which
  9. customwas triturated in ethyl ether

Sources & evidence

ORD record
ord-f303f11fc05b4ab68f21144dbe8bdf7c
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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