Dichloromethane → HCID 73056523, compound

HRID 2284429Notes

Reaction equation

HRID 2284429 reaction equation
[N:1]1([C:7]([NH:9][C:10]2[CH:11]=[C:12]([C:16]3[CH:25]=[N:24][C:23]4[C:22]([N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[N:21][C:20]([C:32]5[CH:33]=[N:34][C:35]([NH:38]C(=O)OC(C)(C)C)=[N:36][CH:37]=5)=[N:19][C:18]=4[CH:17]=3)[CH:13]=[CH:14][CH:15]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(Cl)Cl.C(O)(C(F)(F)F)=O>CO.C(Cl)(Cl)Cl>[NH2:38][C:35]1[N:34]=[CH:33][C:32]([C:20]2[N:21]=[C:22]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[C:23]3[N:24]=[CH:25][C:16]([C:12]4[CH:11]=[C:10]([NH:9][C:7]([N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)=[O:8])[CH:15]=[CH:14][CH:13]=4)=[CH:17][C:18]=3[N:19]=2)=[CH:37][N:36]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86710191HCID 86710191, compound

Product 1

HCID 73056523HCID 73056523, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a 25 mL round bottom flask, tert-butyl (5-(7-(3-(morpholine-4-carboxamido)phenyl)-4-morpholinopyrido[3,2-d]pyrimidin-2-yl)pyrimidin-2-yl)carbamate (0.035 g, 0.00006 mol) and DCM (5 mL) were added. To the same flask, TFA (0.013 g, 0.00012 mol) was added and the mixture stirred at room temperature for 3 hours. The volatiles were evaporated under reduced pressure to provide the crude residue. The crude residue was dissolved in 10% methanol in chloroform and washed with aqueous saturated sodium bicarbonate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by preparative TLC (4% methanol in chloroform, double elution) to provide the title compound (0.015 g, 52%). 1H NMR (400 MHz, DMSO-d6): δ 9.19 (s, 2H), 9.02 (d, J=2.4 Hz, 1H), 8.72 (s, 1H), 8.24 (d, J=2.4 Hz, 1H), 8.04 (t, J=1.6 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.46 (t, J=8.0 Hz, 1H), 7.20 (br s, 2H), 4.52 (br s, 4H), 3.84 (t, J=4.8 Hz, 4H), 3.65 (t, J=4.4 Hz, 4H), 3.48 (t, J=4.8 Hz, 4H): LC-MS (ESI): Calculated mass. 513.2, Observed mass [M+H]+: 514.2 (RT=0.19 min).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customto provide the crude residue
  3. washwashed with aqueous saturated sodium bicarbonate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customto provide the crude product
  8. customThe crude product was purified by preparative TLC (4% methanol in chloroform, double elution)

Sources & evidence

ORD record
ord-c12dee8921514b96a37ab4d1e12e6f43
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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