Sodium borohydride → HCID 90931501, compound

HRID 1093230Notes

Reaction equation

HRID 1093230 reaction equation
[CH3:1][O:2][C:3](=[O:35])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:20]4[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]4)[N:18]=[CH:19][C:14]3=[C:13]([N:27]3[CH2:33][CH:32]4[O:34][CH:29]([CH2:30][CH2:31]4)[CH2:28]3)[N:12]=2)=[CH:7][CH:6]=1.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:35])[NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:20]4[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]4)[N:18]=[CH:19][C:14]3=[C:13]([N:27]3[CH2:33][CH:32]4[O:34][CH:29]([CH2:30][CH2:31]4)[CH2:28]3)[N:12]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 91022940HCID 91022940, compound

Product 1

HCID 90931501HCID 90931501, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl{4-[4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1-(4-oxocyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}carbamate (63 mg) (0.13 mmol) in THF (2.0 mL) was added an excess of sodium borohydride. The mixture was stirred for 1 hr. at 50 C. The reaction was then cooled and quenched with water and extracted three times with EtOAc. Organics were dried (MgSO4) and concentrated in vacuo. The resulting oil was triturated with diethyl ether to give a white solid. The solid was filtered and washed the diethyl ether to give (44 mg) MS m/z=479.2 (M+H).

Workup

  1. temperatureThe reaction was then cooled
  2. customquenched with water
  3. extractionextracted three times with EtOAc
  4. dry with materialOrganics were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil was triturated with diethyl ether
  7. customto give a white solid
  8. filtrationThe solid was filtered
  9. washwashed the diethyl ether
  10. customto give (44 mg)

Sources & evidence

ORD record
ord-32a7d144ef7e4a5481da6539cd023bbd
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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