Hydrochloric Acid → HCID 178523000, compound

HRID 2373507Notes

Reaction equation

HRID 2373507 reaction equation
[OH:1][C:2]1[C:3]([C:14]([O:16]C)=O)=[N:4][C:5]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:6][C:7]=1[OH:8].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.Cl>CN(C=O)C>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:14]([C:3]2[C:2]([OH:1])=[C:7]([OH:8])[N:6]=[C:5]([C:9]3[S:10][CH:11]=[CH:12][CH:13]=3)[N:4]=2)=[O:16])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 673264-FluorobenzylamineHCID 178499075HCID 178499075, compound

Product 1

HCID 178523000HCID 178523000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 5,6-dihydroxy-2-thien-2-ylpyrimidine-4-carboxylate (A-2) was dissolved in DMF and 2.0 eq. of 4-fluorobenzylamine were added to the stirred solution. Reaction mixture was left overnight at 90° C. After cooling to room temperature 1 N HCl was added and a solid precipitated from the mixture. This solid was collected by filtration, washed with ethyl ether and dried under vacuum to afford the compound (A-3). 1H NMR (DMSO-d6, 300 MHz) δ 13.0 (s, 1 H), 12.5 (s, 1H), 9.18 (bs, 1 H), 8.03 (d, J=3.0 Hz, 1 H), 7.81 (d, J=4.8 Hz, 1 H), 7.39 (dd, J=5.7 Hz, J=8.4 Hz, 2 H), 7.19-7.2 (m, 3 H), 4.51 (d, J=6.3 Hz, 2 H).

Workup

  1. customReaction mixture
  2. additionwas added
  3. customa solid precipitated from the mixture
  4. filtrationThis solid was collected by filtration
  5. washwashed with ethyl ether
  6. customdried under vacuum
  7. customto afford the compound (A-3)

Sources & evidence

ORD record
ord-e885ac55e4e34e10994d71da78fbdcf3
Source dataset
uspto-grants-2008_12
Patent number
US07459452B2

Reaction notes

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