Nitrogen → HCID 59484953, compound

HRID 925492Notes

Reaction equation

HRID 925492 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([C:14](=[O:16])[CH3:15])[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1.N#N.[Cl-].[Cl-].[Ca+2].[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26][O:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[C:10]([C:14](=[O:16])[CH3:15])[CH:11]=[CH:12][CH:13]=2)=[N:4][CH:3]=1

Participants

8

Reactant 6

HCID 947NitrogenHCID 11776TriphenylphosphineHCID 766463-(Dimethylamino)-1-propanolHCID 97268Di-tert-butyl azodicarboxylateHCID 5284359Calcium ChlorideHCID 59484956HCID 59484956, compound

Product 1

HCID 59484953HCID 59484953, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.4 g of 1-[3-(5-hydroxypyrimidin-2-yl)phenyl]ethanone (11.2 mmol) are suspended in 40 ml of abs. THF in an N2-flushed apparatus with CaCl2 protection, 1.576 ml of 3-(dimethylamino)-1-propanol (13.44 mmol) and 5.602 g of polymer-bound triphenylphosphine (16.81 mmol) are added, and the mixture is stirred at RT for 30 min. 3.87 g of di-tert-butyl azodicarboxylate (16.81 mmol) are added with ice/H2O cooling and stirring, and the mixture is stirred at RT for a further 2 h. For work-up, the polymer is removed by filtration and rinsed with copious dichloromethane, and the filtrate is extracted 1× with water and 2× with aqueous 1 N HCl. The combined HCl extracts are rendered alkaline using NaOH and extracted 3× with 50 ml of dichloromethane. The dichloromethane extracts are combined, dried over sodium sulfate, evaporated to dryness and crystallised from petroleum ether 40-60; m.p. 61-2° C.

Workup

  1. additionare added
  2. stirringstirring
  3. stirringthe mixture is stirred at RT for a further 2 h
  4. customFor work-up, the polymer is removed by filtration
  5. washrinsed with copious dichloromethane
  6. extractionthe filtrate is extracted 1× with water and 2× with aqueous 1 N HCl
  7. extractionextracted 3× with 50 ml of dichloromethane
  8. dry with materialdried over sodium sulfate
  9. customevaporated to dryness
  10. customcrystallised from petroleum ether 40-60

Sources & evidence

ORD record
ord-3c6810d182d04499bd3203a624c71b07
Source dataset
uspto-grants-2016_03
Patent number
US09284300B2

Reaction notes

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