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Dichloromethane → HCID 73056228, compound

HRID 2284412
Notes
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Reaction equation

HRID 2284412 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:22]=[N:21][C:20]4[C:19]([N:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)=[N:18][C:17]([C:29]5[CH:30]=[N:31][C:32]([NH:35]C(=O)OC(C)(C)C)=[N:33][CH:34]=5)=[N:16][C:15]=4[CH:14]=3)=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1.C(Cl)Cl.C(O)(C(F)(F)F)=O>CO.C(Cl)(Cl)Cl>[NH2:35][C:32]1[N:31]=[CH:30][C:29]([C:17]2[N:18]=[C:19]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[C:20]3[N:21]=[CH:22][C:13]([C:10]4[CH:9]=[CH:8][C:7]([C:5]([NH:4][CH:1]5[CH2:2][CH2:3]5)=[O:6])=[CH:12][CH:11]=4)=[CH:14][C:15]=3[N:16]=2)=[CH:34][N:33]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86710179HCID 86710179, compound

Product 1

HCID 73056228HCID 73056228, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 6212
Chloroform
Solvent

Procedure

To a 50 mL round bottom flask, tert-butyl (5-(7-(4-(cyclopropylcarbamoyl)phenyl)-4-morpholinopyrido[3,2-d]pyrimidin-2-yl)pyrimidin-2-yl)carbamate (0.1 g, 0.00018 mol) and DCM (10 mL) were added. To the same reaction flask, TFA (0.055 mL, 0.00072 mol) was added and the reaction mixture was stirred at room temperature for 12 hours. The volatiles were evaporated under reduced pressure to provide crude residue. The residue was dissolved in 10% methanol in chloroform, washed with saturated sodium bicarbonate solution, brine, dried over sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by flash column chromatography (3-4% methanol in chloroform) to provide the title compound (0.016 g, 12%). 1H NMR (400 MHz, DMSO-d6): δ 9.19 (br s, 2H), 9.12 (d, J=1.6 Hz, 1H), 8.58 (d, J=4.0 Hz, 1H), 8.43 (d, J=1.6 Hz, 1H), 8.07 (d, J=8.4 Hz, 2H), 8.00 (d, J=8.4 Hz, 2H), 7.22 (br s, 2H), 4.52 (br s, 4H), 3.83 (s, 4H), 2.93-2.86 (m, 1H), 0.72 (d, J=5.2 Hz, 2H), 0.61 (d, J=2.4 Hz, 2H): LC-MS (ESI): Calculated mass: 468.2; Observed mass [M+H]+: 469.0. (RT=0.19 min).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customto provide crude residue
  3. washwashed with saturated sodium bicarbonate solution, brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customto provide the crude product
  7. customThe crude product was purified by flash column chromatography (3-4% methanol in chloroform)

Sources & evidence

ORD record
ord-c7bf98eadd9c49dfbab322f006b5a25f
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145411B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes