4,6-Dichloropyrimidine → HCID 86711520, compound

HRID 1771405Notes

Reaction equation

HRID 1771405 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:13])=[CH:5][CH:4]=1.C1CCN2C(=NCCC2)CC1.[Cl:25][C:26]1[CH:31]=[C:30](Cl)[N:29]=[CH:28][N:27]=1>C(#N)C>[Cl:25][C:26]1[N:27]=[CH:28][N:29]=[C:30]([O:13][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([NH2:2])=[CH:4][CH:5]=2)[CH:31]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27238584-Amino-1-naphthol hydrochloride

Product 1

HCID 86711520HCID 86711520, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-aminonaphthalen-1-ol hydrochloride (6.82 g, 31.4 mmol) in acetonitrile (80 mL) at 0° C. was added drop-wise DBU (11.0 mL, 75.0 mmol). After 10 min 4,6-dichloropyrimidine (5.00 g, 34.0 mmol) was added portion-wise over 5 min and the reaction mixture warmed to RT for 3 hr and then evaporated in vacuo. The residue was diluted with water (250 mL) and sonicated for 15 min and then stirred at RT for 16 hr. The resulting precipitate was isolated by filtration, washed with water (3×100 mL) and dried in vacuo to afford the title compound, Intermediate E3, as a grey solid (8.27 g, 97%); Rt 1.85 min (Method 2, acidic); m/z 272 (M+H)+, (ES+).

Workup

  1. customevaporated in vacuo
  2. additionThe residue was diluted with water (250 mL)
  3. customsonicated for 15 min
  4. customThe resulting precipitate was isolated by filtration
  5. washwashed with water (3×100 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-78f48944e29d433eaed5e7e6190af2fc
Source dataset
uspto-grants-2016_02
Patent number
US09249125B2

Reaction notes

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