Picolinic acid → US9296747, Example 15

HRID 930513Notes

Reaction equation

HRID 930513 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:43][O:44][C:45]1[CH:46]=[C:47]([NH:55][C:56]2[N:57]=[CH:58][C:59]3[CH2:65][NH:64][CH2:63][CH2:62][C:60]=3[N:61]=2)[CH:48]=[C:49]([O:53][CH3:54])[C:50]=1[O:51][CH3:52]>CN(C=O)C.CCOC(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([N:64]1[CH2:63][CH2:62][C:60]2[N:61]=[C:56]([NH:55][C:47]3[CH:46]=[C:45]([O:44][CH3:43])[C:50]([O:51][CH3:52])=[C:49]([O:53][CH3:54])[CH:48]=3)[N:57]=[CH:58][C:59]=2[CH2:65]1)=[O:9]

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118970894N-(3,4,5-Trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 118970903US9296747, Example 15

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-picolinic acid (40.6 mg, 0.33 mmol), N, N-diisopropylethylamine (0.105 mL, 0.60 mmol), and HBTU (125 mg, 0.33 mmol) in DMF (2.0 mL) was stirred at room temperature for 5 minutes, then N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine, Intermediate 1 (94.8 mg, 0.30 mmol; see Syntheses of Starting Materials section for prep) added and the reaction continued for 1.5 hours at rt. The reaction mixture was treated with an EtOAc/aqueous Na2CO3(aq) solution work-up to give an orange oil. The oil was chromatographed eluting with 5% MeOH in 1:1 EtOAc/CHCl3 giving an off-white solid (107 mg, 85%).

Workup

  1. waitthe reaction continued for 1.5 hours at rt
  2. customto give an orange oil
  3. customThe oil was chromatographed
  4. washeluting with 5% MeOH in 1:1 EtOAc/CHCl3 giving an off-white solid (107 mg, 85%)

Sources & evidence

ORD record
ord-0c22c7c55875402c95de70a4be689f76
Source dataset
uspto-grants-2016_03
Patent number
US09296747B1

Reaction notes

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