1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(2-Methyl-1H-indol-5-yloxy)-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester

HRID 884530Notes

Reaction equation

HRID 884530 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](=[O:18])[NH:13][CH:12]=[N:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1CCN2C(=NCCC2)CC1.[CH3:63][C:64]1[NH:65][C:66]2[C:71]([CH:72]=1)=[CH:70][C:69](O)=[CH:68][CH:67]=2>>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([O:18][C:69]3[CH:70]=[C:71]4[C:66](=[CH:67][CH:68]=3)[NH:65][C:64]([CH3:63])=[CH:72]4)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 833362-methyl-1H-indol-5-olHCID 2724699PyBOPHCID 135741723tert-butyl 4-hydroxy-5H,6H,7H,8H-pyrido[3,4-d]pyrimidine-7-carboxylate

Product 1

HCID 593946124-(2-Methyl-1H-indol-5-yloxy)-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester

Procedure

To a stirring solution of 4-oxo-4,5,6,8-tetrahydro-3H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester, Example 31-A, (300 mg, 1.2 mmol) in I (5 mL) is added PyBOP (800 mg, 1.55 mmol) and DBU (0.2 mL, 1.43 mmol). After 20 min 2-methyl-1H-indol-5-ol (211 mg, 1.43 mmol) is added. The mixture is then stirred at room temperature for 16 h. At that point the reaction is concentrated under reduced pressure and the residue is dissolved in EtOAc and washed by water and brine. The organic layer is dried over sodium sulfate, concentrated under reduced pressure. The residue is purified by FCC (EtOAc/heptane from 0% to 40%) to give the title compound. MS (ESI) m/z 381.0 (M+1).

Workup

  1. concentrationAt that point the reaction is concentrated under reduced pressure
  2. dissolutionthe residue is dissolved in EtOAc
  3. washwashed by water and brine
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by FCC (EtOAc/heptane from 0% to 40%)

Sources & evidence

ORD record
ord-81adde30b8584fa0aac3978440b4ab44
Source dataset
uspto-grants-2012_08
Patent number
US08242125B2

Reaction notes

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