Methanol → HCID 135774036, compound

HRID 231516Notes

Reaction equation

HRID 231516 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[CH:15][C:16]([C:17]#[N:18])=[C:12]3[N:11]=[C:10]([CH3:19])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.O1CCCC1.CO.[BH4-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[N:13]3[N:14]=[CH:15][C:16]([C:17]#[N:18])=[C:12]3[NH:11][CH:10]([CH3:19])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 14501869HCID 14501869, compound

Product 1

HCID 135774036HCID 135774036, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an unweighed amount of 7-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile (prepared as described in Ex. 14) in a stirred mixture of one liter of tetrahydrofuran and one liter of methyl alcohol, under nitrogen was added 20.0 g of sodium borohydride, portionwise. The mixture was stirred for 8 hours at room temperature, then allowed to stand for 3 days providing two layers. The top layer was separated, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo to give a yellow oil. The oil was dissolved in 250 ml of chloroform and filtered through hydrous magnesium silicate and evaporated to a yellow oil. The oil was triturated with ether, forming crystals on scratching. The crystals were collected to give the desired product as white crystals, mp 192°-195° C.

Workup

  1. waitto stand for 3 days
  2. customproviding two layers
  3. customThe top layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. customto give a yellow oil
  8. filtrationfiltered through hydrous magnesium silicate
  9. customevaporated to a yellow oil
  10. customThe oil was triturated with ether
  11. customforming crystals
  12. customThe crystals were collected

Sources & evidence

ORD record
ord-b7f6c9afaea848ca80b4199c6c1db784
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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