(S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine → HCID 178461589, compound

HRID 1626596Notes

Reaction equation

HRID 1626596 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([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:4][CH:3]=1.Cl[C:28]1[N:29]=[C:30]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][C@@H:39]2[CH3:44])[C:31]2[CH2:36][N:35]([CH3:37])[CH2:34][C:32]=2[N:33]=1>>[OH:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:28]3[N:29]=[C:30]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][C@@H:39]4[CH3:44])[C:31]4[CH2:36][N:35]([CH3:37])[CH2:34][C:32]=4[N:33]=3)=[CH:16][CH:17]=2)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 86663154(S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine2×HCID 178431079HCID 178431079, compound

Product 1

HCID 178461589HCID 178461589, compoundYield 9.2%

Procedure

Method as described for example 47 using 1-(6-hydroxypyridin-2-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea and (S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine (intermediate 12) as starting materials. The reaction mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with MeOH and reduced in vacuo. The residue was purified by prep LCMS (high pH), to yield the title compound (7.9 mg, 0.017 mmol, 9.2%).

Workup

  1. filtrationThe reaction mixture was filtered through a celite 545 pre-packed cartridge (2.5 g)
  2. washwashed with MeOH
  3. customThe residue was purified by prep LCMS (high pH)

Sources & evidence

ORD record
ord-8dc30c1efe114b5c875b0e97af69a5d9
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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