Dimethylformamide → HCID 122463792, compound

HRID 1479935Notes

Reaction equation

HRID 1479935 reaction equation
[OH:1][CH2:2][C:3]1[C:4](=[O:10])[NH:5][C:6](=[O:9])[NH:7][CH:8]=1.[C:11]([OH:18])(=[O:17])/[CH:12]=[CH:13]/[C:14]([OH:16])=O.CCN=C=NC[CH2:25][CH2:26]N(C)C.C[N:31]([C:33]([O:37]N1N=NC2C=CC=CC1=2)=[N+:34]([CH3:36])C)[CH3:32].F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.CN(C=[O:65])C>ClCCl>[O:9]=[C:6]1[NH:5][C:4](=[O:10])[C:3]([CH2:2][O:1][C:14](=[O:16])/[CH:13]=[CH:12]/[C:11]([O:18][CH2:25][C:26]2[C:36](=[O:65])[NH:34][C:33](=[O:37])[NH:31][CH:32]=2)=[O:17])=[CH:8][NH:7]1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 781685-(Hydroxymethyl)uracilHCID 444972Fumaric AcidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 122463792HCID 122463792, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-(Hydroxymethyl)-1H-pyrimidine-2,4-dione (3.0 eq) was added to a mixture of fumaric acid (1.0 g, 1.0 eq), EDAC (or HBTU) (4.0 eq) and triethylamine (6.0 eq) in dichloromethane (or DMF) (50 mL). The mixture was stirred at 0° C. for 1 h and then at 20° C. overnight. The reaction was concentrated in vacuo to a residue and then purified by reverse-phase (C-18) liquid chromatography using water and acetonitrile as eluents to yield compound (6). MS (ESI): m/z 365.1 (M+H)+.

Workup

  1. customat 20° C.
  2. customovernight
  3. concentrationThe reaction was concentrated in vacuo to a residue
  4. custompurified by reverse-phase (C-18) liquid chromatography

Sources & evidence

ORD record
ord-57783a8e59434a459aeed1addb2f6cb8
Source dataset
uspto-grants-2016_08
Patent number
US09409872B1

Reaction notes

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