Potassium Carbonate → HCID 86710190, compound

HRID 2284428Notes

Reaction equation

HRID 2284428 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:34]=[N:33][C:32]3[C:31]([N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)=[N:30][C:29]([C:41]4[CH:42]=[N:43][C:44]([NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[N:45][CH:46]=4)=[N:28][C:27]=3[CH:26]=2)[CH:22]=[CH:23][CH:24]=1)=[O:17]>CN(C=O)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:15][C:16]([NH:18][C:19]2[CH:20]=[C:21]([C:25]3[CH:34]=[N:33][C:32]4[C:31]([N:35]5[CH2:40][CH2:39][O:38][CH2:37][CH2:36]5)=[N:30][C:29]([C:41]5[CH:42]=[N:43][C:44]([NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[N:45][CH:46]=5)=[N:28][C:27]=4[CH:26]=3)[CH:22]=[CH:23][CH:24]=2)=[O:17])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 86710189HCID 86710189, compound

Product 1

HCID 86710190HCID 86710190, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

To a 25 mL round bottom flask, 4-hydroxy piperidine (0.021 g, 0.00021 mol) and DMF (1.5 mL) were added and then cooled to 0-10° C. To the same reaction flask, potassium carbonate (0.058 g, 0.00042 mol) was added and the reaction mixture was stirred at 0-10° C. for 30 minutes. To the same flask, a solution of tert-butyl (5-(7-(3-(2-chloroacetamido)phenyl)-4-morpholinopyrido[3,2-d]pyrimidin-2-yl)pyrimidin-2-yl)carbamate (0.08 g, 0.00014 mol) in DMF (1 mL) was added and then stirred at room temperature for 12 hours. The reaction was quenched with water to provide the precipitate. The precipitate was collected by filtration to provide the title compound (0.078 g, 88%). The compound was used in the next step without purification. 1H NMR (300 MHz, DMSO-d6): δ 10.43 (s, 1H), 9.84 (s, 1H), 9.49 (s, 1H), 9.12 (d, J=2.1 Hz, 1H), 8.38 (s, J=2.1 Hz, 1H), 8.21 (br s, 1H), 7.87 (d, J=7.8 Hz, 1H), 7.68 (d, J=7.8 Hz, 1H), 7.54 (t, J=8.1 Hz, 1H), 4.63 (d, J=3.9 Hz, 1H), 4.58 (br s, 4H), 3.84 (s, 4H), 3.51-3.49 (m, 1H), 3.28 (s, 2H), 3.13-2.75 (m, 2H), 2.29 (t, J=8.7 Hz, 2H), 1.78 (d, J=9.3 Hz, 2H), 1.58 (d, J=9.3 Hz, 2H), 1.49 (s, 9H): LCMS (ESI): Calculated. 641.3, Observed mass [M+H]+: 642.2, (RT=0.22 min).

Workup

  1. stirringstirred at room temperature for 12 hours
  2. customThe reaction was quenched with water
  3. customto provide the precipitate
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5439b24b30ac4e3ebdf10ef035359489
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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