1-(3-Hydroxyphenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → (S)-ethyl 2-(4-(3-(3-hydroxyphenyl)ureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626625Notes

Reaction equation

HRID 1626625 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl[C:28]1[N:29]=[C:30]([N:42]2[CH2:47][CH2:46][O:45][CH2:44][C@@H:43]2[CH3:48])[C:31]2[CH2:36][N:35]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:34][C:32]=2[N:33]=1>>[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:10])[NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:28]3[N:29]=[C:30]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][C@@H:43]4[CH3:48])[C:31]4[CH2:36][N:35]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:34][C:32]=4[N:33]=3)=[CH:16][CH:17]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 161252281-(3-Hydroxyphenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66679039(S)-ethyl 2-(4-(3-(3-hydroxyphenyl)ureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Procedure

Method as intermediate 5 using 1-(3-hydroxyphenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea and (S)-ethyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 11) as starting materials. Reaction mixture was concentrated in vacuo and purified by prep. HPLC (low pH) to afford a brown solid, 22 mg (8% over 2 steps).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by prep
  4. customHPLC (low pH) to afford a brown solid, 22 mg (8% over 2 steps)

Sources & evidence

ORD record
ord-2f341700788146af8314817a4711eac6
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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