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Triethylamine → HCID 178478262, compound

HRID 541849
Notes
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Reaction equation

HRID 541849 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6](/[CH:10]=[CH:11]\[C:12]2[CH:13]=[C:14]([NH:18][C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21](Cl)[N:20]=3)[CH:15]=[CH:16][CH:17]=2)[CH:5]=1.C(N(CC)CC)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:25][C:24]1[CH:23]=[N:22][C:21]2[NH:3][C:4]3[CH:9]=[CH:8][N:7]=[C:6]([CH:5]=3)[CH:10]=[CH:11][C:12]3[CH:13]=[C:14]([NH:18][C:19]=1[N:20]=2)[CH:15]=[CH:16][CH:17]=3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86636271N-{3-[(Z)-2-(4-Aminopyridin-2-yl)vinyl]phenyl}-2,5-dichloropyrimidin-4-amine Dihydrochloride

Product 1

HCID 178478262HCID 178478262, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of N-{3-[(Z)-2-(4-aminopyridin-2-yl)vinyl]phenyl}-2,5-dichloropyrimidin-4-amine dihydrochloride (34.6 mg, 0.08 mmol) and triethylamine (0.034 mL, 0.24 mmol) in dry 1,4-dioxane (0.70 mL) was added (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.8 mg, 0.0048 mmol), palladium acetate (0.7 mg, 0.003 mmol) and cesium carbonate (52.3 mg, 0.16 mmol). The mixture was degassed by bubbling N2 through the solution. The sealed tube was then microwaved at 150° C. for 30 min. The reaction mixture was diluted with THF/MeOH, filtered and concentrated to give the residue, which was then triturated with MeOH/EtOAc/THF to provide the desired product as a light yellow powder (9 mg, 35%). LCMS for C17H13ClN5 (M+H)+: m/z=322.0. 1H NMR (300 MHz, DMSO-d6): δ 9.81 (s, 1H), 9.33 (s, 1H), 9.15 (s, 1H), 8.49 (s, 1H), 8.26 (m, 1H), 8.19 (s, 1H), 7.33 (m, 1H), 7.24 (m, 1H), 7.08 (d, J=5.7 Hz, 1H), 6.93 (dd, J=5.7, 2.1 Hz, 1H), 6.83 (m, 1H), 6.58 (d, J=13.5 Hz, 1H).

Workup

  1. customThe mixture was degassed
  2. customby bubbling N2 through the solution
  3. customThe sealed tube was then microwaved at 150° C. for 30 min
  4. additionThe reaction mixture was diluted with THF/MeOH
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the residue, which
  8. customwas then triturated with MeOH/EtOAc/THF

Sources & evidence

ORD record
ord-2be50dd881c74e9693c1ea7436fd77ab
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871753B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes