Lithium borohydride → HCID 56932819, compound

HRID 577295Notes

Reaction equation

HRID 577295 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH2:17][C:18]4[CH:19]=[C:20]([N:24]5[CH2:29][CH2:28][O:27][CH2:26][C:25]5=[O:30])[CH:21]=[CH:22][CH:23]=4)[N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1.[BH4-].[Li+]>CO>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH2:17][C:18]4[CH:19]=[C:20]([N:24]5[CH2:29][CH2:28][O:27][CH2:26][CH:25]5[OH:30])[CH:21]=[CH:22][CH:23]=4)[N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 56932316HCID 56932316, compound

Product 1

HCID 56932819HCID 56932819, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(3-((6-(1-methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)morpholin-3-one (45 mg, 0.12 mmol) in 4 mL methanol was added lithium borohydride (170 mg, 70 eq in seven portions every 10 min). The reaction mixture was evaporated and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate, the combined organic phases dried over sodium sulfate and evaporated. The residue was purified with the preparative HPLC to yield the title compound (5 mg, 12 μmol, 10%). 1H NMR (d6-DMSO) δ 8.22 (s, 1H), 7.78 (s, 1H), 7.37-7.32 (m, 3H), 7.29-7.24 (m, 1H), 7.12-7.08 (m, 1H), 7.01 (s, 1H), 6.06 (s, 1H), 5.16 (s, 2H), 4.45 (s, 2H), 4.18 (s, 2H), 3.96-3.91 (m, 2H), 3.76 (s, 3H), 3.68-3.63 (m, 2H); LC-MS method B, (ES+) 407.2, RT=4.04 min.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe combined organic phases dried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified with the preparative HPLC

Sources & evidence

ORD record
ord-764afc230a104bafb35fddc1016087fc
Source dataset
uspto-grants-2015_05
Patent number
US09040545B2

Reaction notes

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