5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine → (S)-ethyl-2-(5-(3-ethylureido)pyrazin-2-yl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626630Notes

Reaction equation

HRID 1626630 reaction equation
C(NC(=O)NC1C=CC([C:12]2[N:13]=[C:14]([N:29]3[CH2:34][CH2:33]OC[C@@H]3C)C3C[CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C:16]=3[N:17]=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(C2N=CC(N)=NC=2)[O:61]1>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]>[CH2:50]([O:49][C:47]([N:45]1[CH2:46][C:41]2[C:40]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][C@@H:53]3[CH3:58])=[N:39][C:38]([C:18]3[CH:16]=[N:17][C:12]([NH:13][C:14]([NH:29][CH2:34][CH3:33])=[O:61])=[CH:20][N:19]=3)=[N:43][C:42]=2[CH2:44]1)=[O:48])[CH3:51]

Participants

5

Reactant 3

HCID 179989875-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amineHCID 59239149HCID 59239149, compoundHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66679218(S)-ethyl-2-(5-(3-ethylureido)pyrazin-2-yl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 58%

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), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine as starting materials, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) as catalyst. The reaction 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 flash chromatography using a gradient of 0-40% DCM/MeOH yielding the title compound (69 mg, 0.18 mmol, 58%).

Workup

  1. filtrationThe reaction 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 flash chromatography

Sources & evidence

ORD record
ord-156a9b3514284112882eed945b5c0dd5
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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