Hydrochloric Acid → HCID 24777233, compound

HRID 2060648Notes

Reaction equation

HRID 2060648 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:20]=1[Cl:26])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.COCCO.Cl>O>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:20]([Cl:26])[CH:21]=2)[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80192-MethoxyethanolHCID 842305-Pyrimidinecarboxaldehyde, 4-amino-6-chloro-HCID 12682854-Benzyloxy-3-chloroaniline

Product 1

HCID 24777233HCID 24777233, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 3-necked round bottom flask equipped with a thermal couple, an overhead stirrer and a condenser was added 4-amino-6-chloro-pyrimidine-5-carbaldehyde Cpd 1a (3.23 g, 19.0 mmol), 4-benzyloxy-3-chloro-phenylamine Cpd 1b (4.24 g, 18.1 mmol), 2-methoxyethanol (27 ml) and water (3 ml). The mixture was stirred at room temperature and a 6N HCl solution (0.30 ml, 0.10 eq.) was added. The mixture was heated to 80° C. for 1-2 hours until the starting materials were consumed. The mixture was cooled to room temperature and 6 N NaOH solution (3.3 ml) and water (8 ml) were added. The mixture was cooled to room temperature again and the solid was collected by vacuum filtration. The reaction flask was rinsed by 1:1 EtOH:water (2×10 ml) and the rinses were used to wash the filter cake. The filter cake was further washed by 1:1 EtOH:water (2×10 ml), suction dried, dried in an vacuum oven at 60° C. under house vacuum to afford the title Compound 1c free base as a light yellow solid (6.06 g). 1H NMR (400 MHz, DMSO-d6) δ 10.66 (s, 1H), 10.14 (s, 1H), 8.11 (s, 1H), 7.90 (bs, 1H), 7.88 (d, J=2.0 Hz, 1H), 7.48-7.32 (m, 5H), 7.21 (d, J=8.0 Hz, 1H), 5.20 (s, 2H), 3.24 (bs, 2H); mp 206° C. (by DSC).

Workup

  1. customIn a 3-necked round bottom flask equipped with a thermal couple, an overhead stirrer and a condenser
  2. temperatureThe mixture was heated to 80° C. for 1-2 hours until the starting materials
  3. customwere consumed
  4. temperatureThe mixture was cooled to room temperature
  5. addition6 N NaOH solution (3.3 ml) and water (8 ml) were added
  6. temperatureThe mixture was cooled to room temperature again
  7. filtrationthe solid was collected by vacuum filtration
  8. washThe reaction flask was rinsed by 1:1 EtOH
  9. washto wash the filter cake
  10. washThe filter cake was further washed by 1:1 EtOH
  11. dry with materialwater (2×10 ml), suction dried
  12. customdried in an vacuum oven at 60° C. under house vacuum

Sources & evidence

ORD record
ord-94f0d06566b44729a5f832d2d10e152e
Source dataset
uspto-grants-2012_10
Patent number
US08278446B2

Reaction notes

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