Methanol → HCID 78031603, compound

HRID 1507765Notes

Reaction equation

HRID 1507765 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:12]([C:14]1[CH:19]=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH:15]=1)[CH3:13])([CH3:4])([CH3:3])[CH3:2].[NH2:37][C:38]1[C:43]([I:44])=[CH:42][NH:41][C:40](=[O:45])[N:39]=1.CO.CN(C)CCN(C)C>CC([O-])=O.CC([O-])=O.[Cu+2].O>[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:12]([C:14]1[CH:15]=[CH:16][C:17]([N:41]2[CH:42]=[C:43]([I:44])[C:38]([NH2:37])=[N:39][C:40]2=[O:45])=[CH:18][CH:19]=1)[CH3:13])[C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 78031019HCID 78031019, compoundHCID 178509022HCID 178509022, compound

Product 1

HCID 78031603HCID 78031603, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

Cu(OAc)2 (6.02 g, 33.13 mmol, 1.1 eq.) was added to a mixture of [3-(tert-butoxycarbonyl-{1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-amino)-propyl]-carbamic acid tert-butyl ester (15.18 g, 30.12 mmol, 1 eq.), 4-amino-5-iodo-1H-pyrimidin-2-one (7.85 g, 33.13 mmol, 1.1 eq.), MeOH (400 mL) and H2O (100 mL), followed by N,N,N′,N′-tetramethyl-ethane-1,2-diamine (7.69 g, 66.26 mmol, 2.2 eq.). The Mixture was stirred at RT under air for 48 h (weekend) before concentrated to a volume ca. 130 mL. The residue was diluted with CH2Cl2 (200 mL). The CH2Cl2 extract was washed with brine and concentrated. The crude product was purified by flash chromatography (CH2Cl2:MeOH:NH4OH/35:1:0.01) to afford [3-({1-[4-(4-amino-5-iodo-2-oxo-2H-pyrimidin-1-yl)-phenyl]-ethyl}-tert-butoxycarbonyl-amino)-propyl]-carbamic acid tert-butyl ester (16.06 g, 87%).

Workup

  1. concentrationbefore concentrated to a volume ca. 130 mL
  2. additionThe residue was diluted with CH2Cl2 (200 mL)
  3. extractionThe CH2Cl2 extract
  4. washwas washed with brine
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (CH2Cl2:MeOH:NH4OH/35:1:0.01)

Sources & evidence

ORD record
ord-ac86f67538434065b714cbd35759d5d4
Source dataset
uspto-grants-2015_12
Patent number
US09221827B2

Reaction notes

Loading…