4-Methylmorpholine → HCID 178509063, compound

HRID 348488Notes

Reaction equation

HRID 348488 reaction equation
[K].[NH2:2][C:3]1[C:8]([C:9]([O-:11])=O)=[CH:7][N:6]=[C:5]([S:12]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:56][C:57]1[CH:63]=[CH:62][C:60]([NH2:61])=[CH:59][CH:58]=1.CN1CCOCC1>CN1C(=O)CCC1.O>[F:56][C:57]1[CH:63]=[CH:62][C:60]([NH:61][C:9]([C:8]2[C:3]([NH2:2])=[N:4][C:5]([SH:12])=[N:6][CH:7]=2)=[O:11])=[CH:59][CH:58]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 97314-FluoroanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86760401HCID 86760401, compound

Product 1

HCID 178509063HCID 178509063, compoundYield 490%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Solid portions of potassium-4-amino-2-tritylsulfanylpyrimidine-5-carboxylate (46 g, 10 mmol) followed by HATU (39 g, 0.10 mol) were added, at ambient temperature, to a solution of 4-fluoroaniline (11 g, 0.10 mol) and NMM (31 g, 0.30 mol) in NMP (500 mL). After stirring for 12 hours, the resulting orange solution was poured into water (1000 mL) and the oily, solid precipitant was collected, dissolved in dichloromethane (500 mL), and diluted with acetic acid (50 mL). The resulting solution was stirred (ambient temperature, 3 h), then concentrated in vacuo (to about 150 mL total volume) and diluted with diethyl ether (100 mL). The resulting yellow solid was collected, washed with dichloromethane and dried in vacuo to afford the titled compound (13 g, 49 mmol, 49% yield). 1H NMR (300 MHz, CD3OD) δ 8.20 (s, 1H), 7.58 (dd, J=9.3, 4.8 Hz, 2H), 7.07 (app. t, J=9.0 Hz, 2H); MS (+APCI) m/z 265 (MH+, 100).

Workup

  1. customthe oily, solid precipitant was collected
  2. dissolutiondissolved in dichloromethane (500 mL)
  3. additiondiluted with acetic acid (50 mL)
  4. stirringThe resulting solution was stirred (ambient temperature, 3 h)
  5. concentrationconcentrated in vacuo (to about 150 mL total volume)
  6. additiondiluted with diethyl ether (100 mL)
  7. customThe resulting yellow solid was collected
  8. washwashed with dichloromethane
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b226186305a24b3b949a35be05ed1de2
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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