Triethylamine → (S)-1-(3-hydroxypropyl)-3-(4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1626565Notes

Reaction equation

HRID 1626565 reaction equation
[CH3:1][N:2]1[CH2:10][C:9]2[C:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]3[CH3:17])=[N:7][C:6]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])OC4C=CC=CC=4)=[CH:20][CH:19]=3)=[N:5][C:4]=2[CH2:3]1.CCN(CC)CC.[NH2:41][CH2:42][CH2:43][CH2:44][OH:45]>CN(C=O)C>[OH:45][CH2:44][CH2:43][CH2:42][NH:41][C:25]([NH:24][C:21]1[CH:20]=[CH:19][C:18]([C:6]2[N:7]=[C:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]3[CH3:17])[C:9]3[CH2:10][N:2]([CH3:1])[CH2:3][C:4]=3[N:5]=2)=[CH:23][CH:22]=1)=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 66678768(S)-phenyl 4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenylcarbamate2×

Product 1

HCID 46912595(S)-1-(3-hydroxypropyl)-3-(4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)ureaYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of (S)-phenyl 4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenylcarbamate (intermediate 10) (50 mg, 0.12 mmol) in dry DMF, was added Et3N (51 μL, 0.36 mmol) and 3-aminopropan-1-ol (42 μL, 0.56 mmol). The reaction mixture was then heated at 50° C. for 2 hours. The solvent was then removed in vacuo and the crude residue was purified by prep. LCMS (high pH) affording the title compound as clear oil (12.5 mg, 0.029 mmol, 26%).

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe crude residue was purified by prep

Sources & evidence

ORD record
ord-42a257a2fe3246e19274baeab8f78ec2
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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