Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → Phenyl[4,5,6,7-tetrahydro-7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone

HRID 231513Notes

Reaction equation

HRID 231513 reaction equation
[C:1]1([C:7]([C:9]2[CH:10]=[N:11][N:12]3[C:17]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[CH:16][CH:15]=[N:14][C:13]=23)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>C(O)(=O)C>[C:1]1([C:7]([C:9]2[CH:10]=[N:11][N:12]3[CH:17]([C:18]4[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=4)[CH2:16][CH2:15][NH:14][C:13]=23)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 5003444Sodium cyanoborohydrideHCID 13475885Phenyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone

Product 1

HCID 135671371Phenyl[4,5,6,7-tetrahydro-7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 20.0 g portion of phenyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone (prepared as described in Ex. 9) suspended and stirred in 100 ml of glacial acetic acid under nitrogen was added in portions 8.5 g of sodium cyanoborohydride, during this addition another 50 ml of glacial acetic was also added. After 3 hours the solution was evaporated to dryness in vacuo. The residue was dissolved in dichloromethane and treated with saturated sodium bicarbonate until basic. The organic layer was separated and dried over anhydrous sodium sulfate. Evaporation gave a gummy solid. The solid was recrystallized from isopropyl alcohol and gave the desired product as a light yellow solid, mp 186°-189° C.

Workup

  1. additionwas also added
  2. customAfter 3 hours the solution was evaporated to dryness in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. additiontreated with saturated sodium bicarbonate until basic
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation
  8. customgave a gummy solid
  9. customThe solid was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-6962e40379c84af4bb39093bf3f1d510
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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