1-Propyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → (S)-1-(4-(6-(cyclopropylmethyl)-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)-3-propylurea

HRID 1626561Notes

Reaction equation

HRID 1626561 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[C:5]2[CH2:10][N:9]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[CH2:8][C:6]=2[N:7]=1.[CH2:22]([NH:25][C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][CH:30]=1)=[O:27])[CH2:23][CH3:24]>>[CH:12]1([CH2:11][N:9]2[CH2:10][C:5]3[C:4]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]4[CH3:21])=[N:3][C:2]([C:32]4[CH:31]=[CH:30][C:29]([NH:28][C:26]([NH:25][CH2:22][CH2:23][CH3:24])=[O:27])=[CH:34][CH:33]=4)=[N:7][C:6]=3[CH2:8]2)[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 441195781-Propyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 86663153(S)-4-(2-chloro-6-(cyclopropylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

Product 1

HCID 46912497(S)-1-(4-(6-(cyclopropylmethyl)-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)-3-propylurea

Procedure

Method as described for example 47 using intermediate 8 and 1-propyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea as starting materials. Purified by prep. LCMS (low pH).

Workup

  1. customPurified by prep

Sources & evidence

ORD record
ord-1ea489bde68e46c48b564e68d3495e61
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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