Dimethylamine → HCID 178484582, compound

HRID 2052989Notes

Reaction equation

HRID 2052989 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:12]=3)=[CH:9][N:8]([C@@H:25]3[CH2:28][C@H:27]([C:29](O)=[O:30])[CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1.F[B-](F)(F)F.O=[C:38]1C=CC=[CH:40][N:39]1OC(N(C)C)=[N+](C)C.C(N(C(C)C)CC)(C)C.CNC>CN(C)C=O>[CH3:38][N:39]([CH3:40])[C:29]([C@H:27]1[CH2:28][C@@H:25]([N:8]2[C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=3[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:12]=3)=[CH:9]2)[CH2:26]1)=[O:30]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 178508605HCID 178508605, compound

Product 1

HCID 178484582HCID 178484582, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 45 mg (0.11 mmol) of cis-3-[4-amino-5-(3benzyloxy-phenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid in 2 ml of N,N-dimethylformamide is added 36 mg (0.12 mmol) of O-(1,2-dihydro-2-oxo-1-pyridyl)-1,1,3,3-tetramethyluronium tetrafluoroborate and 39 μl (0.23 mmol) of diisopropylethylamine. 40 μl of a 5.6 M solution of dimethylamine are added thereto. After stirring the solution for 15 min at RT, working-up is effected by partitioning between water and ethyl acetate. The organic layer is dried over magnesium sulfate and concentrated in vacuo to provide cis-3-[4-amino-5-(3-benzyloxy-phenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid dimethylamide. Analytical HPLC: tR=6.81 min (Grad 2); ES-MS: m/eo=442.0.

Workup

  1. customby partitioning between water and ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31731bef885649d384d354d581ba3a59
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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