Phthalimide → HCID 66803653, compound

HRID 2366242Notes

Reaction equation

HRID 2366242 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8]O)[CH:3]=1.[C:10]1(=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[NH:11]1.P(CCCC)(CCCC)CCCC.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][N:11]2[C:12](=[O:19])[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]2=[O:20])[CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 13831TributylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 21934615(6-Aminopyrimidin-4-yl)methanol

Product 1

HCID 66803653HCID 66803653, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of (6-aminopyrimidin-4-yl)methanol (1.0 g, 8.0 mmol), isoindoline-1,3-dione (1.4 g, 9.6 mmol), n-Bu3P (2.42 g, 12.0 mmol) in dry DMF (20 mL) at room temperature was added diisopropyl azodicarboxylate (2.42 g, 12.0 mmol) dropwise. After addition, the resulting mixture was allowed to stir at 80° C. for 48 hours. Solvents were removed under reduced pressure and the residue was purified via chromatography column on silica gel eluting with a 2% gradient of methanol in dichloromethane to give the desired target as a gray solid (0.60 g, 30% yield). 1H-NMR (500 MHz, DMSO-d6): δ 8.22 (s, 1H), 7.95-7.88 (m, 4H), 6.85 (s, 2H), 6.28 (s, 1H), 4.63 (s, 2H). LCMS (ESI) Method B: RT=3.23 min, m/z 233.1 [M+H+].

Workup

  1. additionAfter addition
  2. customSolvents were removed under reduced pressure
  3. customthe residue was purified via chromatography column on silica gel eluting with a 2% gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-d2e941c869b14f0283ed128ec5fe679d
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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