Sodium borohydride → 6-(Hydroxymethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64362
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)=[N:5][N:6]2[CH:11]=[C:10]([C:12](OCC)=[O:13])[CH:9]=[N:8][C:7]=12)#[N:2].[BH4-].[Na+]>C(Cl)Cl.CO>[OH:13][CH2:12][CH:10]1[CH2:11][N:6]2[N:5]=[C:4]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[C:3]([C:1]#[N:2])=[C:7]2[NH:8][CH2:9]1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 117668240Ethyl 3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylate

Produkt 1

HCID 1369281006-(Hydroxymethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carbonitrileAusbeute 111 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylate (250 mg, 0.65 mmol) in DCM (5 mL) and CH3OH (5 mL) was added NaBH4 (250 mg, 6.5 mmol). After stirring at RT for 16 hr, the mixture was partitioned between DCM/CH3OH (100 mL/5 mL) and brine (100 mL). The organic layer was separated from aqueous layers, dried over Na2SO4 and concentrated to afford 250 mg (100%) of 6-(hydroxymethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carbonitrile. MS (ESI) m/e [M+1]+346.9.

Aufarbeitung

  1. customthe mixture was partitioned between DCM/CH3OH (100 mL/5 mL) and brine (100 mL)
  2. customThe organic layer was separated from aqueous layers
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a0f450ec046d4e26a96c4c72cf8f6b19
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447106B2

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