HCID 59239149, compound → (S)-ethyl 2-(4-(3-(2-amino-2-oxoethyl)ureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626628Notes

Reaction equation

HRID 1626628 reaction equation
C(NC(=O)NC1C=CC(C2N=C(N3CCOC[C@@H]3C)C3CCN(C(OC(C)(C)C)=O)CC=3N=2)=CC=1)C.Cl[C:38]1[N:39]=[C:40]([N:52]2[CH2:57][CH2:56][O:55][CH2:54][C@@H:53]2[CH3:58])[C:41]2[CH2:46][N:45]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:44][C:42]=2[N:43]=1.CC1(C)C(C)(C)OB([C:67]2[CH:72]=[CH:71][C:70]([NH:73][C:74](=[O:80])[NH:75][CH2:76][C:77]([NH2:79])=[O:78])=[CH:69][CH:68]=2)O1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:79][C:77](=[O:78])[CH2:76][NH:75][C:74](=[O:80])[NH:73][C:70]1[CH:69]=[CH:68][C:67]([C:38]2[N:39]=[C:40]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][C@@H:53]3[CH3:58])[C:41]3[CH2:46][N:45]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:44][C:42]=3[N:43]=2)=[CH:72][CH:71]=1

Participants

5

Reactant 3

HCID 59239149HCID 59239149, compoundHCID 666870852-(3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureido)acetamideHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66678786(S)-ethyl 2-(4-(3-(2-amino-2-oxoethyl)ureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 12%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Method as described for intermediate 5 using (S)-ethyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 11) and 2-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureido)acetamide as starting materials, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) as catalyst. The mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with MeOH and solvent removed in vacuo. The residue was purified by prep HPLC (high pH) yielding the title compound (10.6 mg, 0.02 mmol, 12%).

Workup

  1. filtrationThe mixture was filtered through a celite 545 pre-packed cartridge (2.5 g)
  2. washwashed with MeOH and solvent
  3. customremoved in vacuo
  4. customThe residue was purified by prep HPLC (high pH)

Sources & evidence

ORD record
ord-6b384ed947354b3cb2c1f66f8d186d01
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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