Triphenylphosphine → HCID 57503761, compound

HRID 2111864Notes

Reaction equation

HRID 2111864 reaction equation
ClC1N=CC2N=C(C)N(C3C=CC(O)=CC=3OC)C(=O)C=2C=1.[Cl:23][C:24]1[N:54]=[CH:53][C:27]2[N:28]=[C:29]([CH3:52])[N:30]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][N:43]4[CH2:48][CH2:47][CH2:46][C@H:45]([CH3:49])[CH2:44]4)=[CH:35][C:34]=3[O:50][CH3:51])[C:31](=[O:32])[C:26]=2[CH:25]=1.C[C@H]1CCCN(CCCO)C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:23][C:24]1[N:54]=[CH:53][C:27]2[N:28]=[C:29]([CH3:52])[N:30]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][N:43]4[CH2:48][CH2:47][CH2:46][C@H:45]([CH3:49])[CH2:44]4)=[CH:35][C:34]=3[O:50][CH3:51])[C:31](=[O:32])[C:26]=2[CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 28351514HCID 28351514, compoundHCID 86600246HCID 86600246, compound

Product 1

HCID 57503761HCID 57503761, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Manufacture of 6-chloro-3-(2-methoxy-4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}phenyl)-2-methylpyrido[3, 4-d]pyrimidin-4(3H)-one 6-chloro-3-(4-hydroxy-2-methoxyphenyl)-2-methylpyrido[3, 4-d]pyrimidin-4(3H)-one (250 mg, 0.79 mmol, 3-[(3S)-3-methylpiperidin-1-yl]propan-1-ol (186 mg, 1.2 mmol) and triphenylphosphine (310 mg, 1.2 mmol)-were dissolved in dry tetrahydrofuran (6 mL) in a current of nitrogen, and cooled on an ice bath. Diisopropyl azodicarboxylate (0.23 mL, 1.2 mmol) was dripped in, and stirred for 2 days at room temperature. The mixture was concentrated under reduced pressure, diethyl ether was added, and the solid precipitate was filtered off. The filtrate was concentrated, the product was purified by silica gel column chromatography (chloroform/methanol=100/0-95/5), and the title compound (200 mg, 56%) was thus obtained as colorless crystals.

Workup

  1. temperaturecooled on an ice bath
  2. concentrationThe mixture was concentrated under reduced pressure, diethyl ether
  3. additionwas added
  4. filtrationthe solid precipitate was filtered off
  5. concentrationThe filtrate was concentrated
  6. customthe product was purified by silica gel column chromatography (chloroform/methanol=100/0-95/5)

Sources & evidence

ORD record
ord-fe5b54bea2ac4bf69002ad9d21e83e2d
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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