Acetone → HCID 66678807, compound

HRID 1626697Notes

Reaction equation

HRID 1626697 reaction equation
Cl.[CH:2]1([NH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]=[C:17]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]4[CH3:30])[C:18]4[CH2:23][NH:22][CH2:21][C:19]=4[N:20]=3)=[C:11]([F:31])[CH:10]=2)=[O:7])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:39][C:40]([CH3:42])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[CH:2]1([NH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]=[C:17]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]4[CH3:30])[C:18]4[CH2:23][N:22]([CH:40]([CH3:42])[CH3:39])[CH2:21][C:19]=4[N:20]=3)=[C:11]([F:31])[CH:10]=2)=[O:7])[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 66687973HCID 66687973, compound

Product 1

HCID 66678807HCID 66678807, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (S)-1-cyclopropyl-3-(3-fluoro-4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (example 149) (115 mg, 0.279 mmol) in anhydrous DMF (2 ml) was added triethylamine (780, 0.558 mmol) and anhydrous acetone (100 μL). The reaction was stirred at RT for 30 minutes after which time sodium triacetoxyborohydride (118 mg, 0.558 mmol) was added and the reaction was stirred for a further 2 hours at RT. The reaction was then partitioned between H2O and DCM and the aqueous phase was extracted into DCM. The organic extracts were combined, dried over magnesium sulphate and concentrated in vacuo. The sample was then purified via preparative HPLC at high pH to yield the title compound (16 mg, 13%).

Workup

  1. additionwas added
  2. customThe reaction was then partitioned between H2O and DCM
  3. extractionthe aqueous phase was extracted into DCM
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe sample was then purified via preparative HPLC at high pH

Sources & evidence

ORD record
ord-6130e20dc6b54fbd82dc0abb4137a213
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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