Triethylamine → HCID 59380000, compound

HRID 2353686Notes

Reaction equation

HRID 2353686 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([O:23]C3C=CC=CC=3)=O)=[CH:16][CH:15]=2)[N:11]=[C:10]([C:30]([O:32][CH3:33])=[O:31])[CH:9]=1.C(N(CC)CC)C.[CH:41]1([NH2:44])[CH2:43][CH2:42]1>CN(C=O)C>[CH:41]1([NH:44][C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([C:12]3[N:11]=[C:10]([C:30]([O:32][CH3:33])=[O:31])[CH:9]=[C:8]([N:3]4[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]4[CH3:1])[N:13]=3)=[CH:15][CH:16]=2)=[O:23])[CH2:43][CH2:42]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 59379902HCID 59379902, compound

Product 1

HCID 59380000HCID 59380000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 6-[(3S)-3-methylmorpholin-4-yl]-2-[4-(phenoxycarbonylamino)phenyl]pyrimidine-4-carboxylate (547 mg) was dissolved in DMF (8 mL) and triethylamine (0.59 mL) followed by cyclopropylamine (0.491 mL) added. The reaction was stirred at 40° C. for 2 hours then the mixture was vacuumed to dryness and partitioned between DCM (50 mL) and water (50 mL). The organic layer was dried over magnesium sulphate and vacuumed to dryness then chromatographed on silica, eluting with 5% methanol in DCM, to give the desired material (351 mg) as a white solid.

Workup

  1. additionadded
  2. custompartitioned between DCM (50 mL) and water (50 mL)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customthen chromatographed on silica
  5. washeluting with 5% methanol in DCM

Sources & evidence

ORD record
ord-3a3dc913d96541d3a871126294a5de05
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

Loading…