Triethylamine → HCID 178476768, compound

HRID 1525211Notes

Reaction equation

HRID 1525211 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[CH3:48][P:49]([C:54]1[CH:59]=[CH:58][C:57]([CH:60]([NH2:67])[C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[CH:56][CH:55]=1)(=[O:53])[O:50][CH2:51][CH3:52]>CC#N>[OH:1][C:2]1[C:7]([C:8]([NH:67][CH:60]([C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)[C:57]2[CH:56]=[CH:55][C:54]([P:49]([CH3:48])(=[O:53])[O:50][CH2:51][CH3:52])=[CH:59][CH:58]=2)=[O:10])=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89462691Ethyl methyl(4-(amino(phenyl)methyl)phenyl)phosphinateHCID 178524750HCID 178524750, compound2×

Product 1

HCID 178476768HCID 178476768, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-hydroxy-2-(pyridin-2-yl)pyrimidine-5-carboxylic acid, 1-1-h (325.5 mg, 1.5 mmol) in MeCN (10 ml) were added HATU (599 mg, 1.51 mmol), Et3N (159 mg, 1.51 mmol) and ethyl methyl(4-(amino(phenyl)methyl)phenyl)phosphinate (2-d′, 433 mg, 1.5 mmol). The resulting mixture was stirred at room temperature for 2 hour. Then it was concentrated under vacuum and the residue was taken into ethyl acetate followed by washing with saturated NH4Cl. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by prep-HPLC to provide the product, 2-4, (159 mg, 22%). 1H NMR (CD3OD, 300 MHz,): δ 8.67 (m, 2H), 8.39 (m, 2H), 7.94 (m, 1H), 7.46 (m, 5H), 7.26 (m, 5H), 6.29 (s, 1H), 3.76 (m, 2H), 1.57 (d, 3H).

Workup

  1. concentrationThen it was concentrated under vacuum
  2. washby washing with saturated NH4Cl
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by prep-HPLC
  6. customto provide the product, 2-4, (159 mg, 22%)

Sources & evidence

ORD record
ord-50548e409ac446acbf91eccded811c60
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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