Water → HCID 178484773, compound

HRID 2169133Notes

Reaction equation

HRID 2169133 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:29]([OH:31])=O)=[N:11][C:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:32]([O:39][CH2:40][CH2:41][NH:42][CH3:43])([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].O=P(Cl)(Cl)Cl.O>N1C=CC=CC=1>[Si:32]([O:39][CH2:40][CH2:41][N:42]([CH3:43])[C:29]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:14]([OH:15])[N:13]=[C:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:11]=1)=[O:31])([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 16203640N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamineHCID 178524878HCID 178524878, compound

Product 1

HCID 178484773HCID 178484773, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-benzyloxy-2-biphenyl-2-ylmethyl-6-hydroxypyrimidine-4-carboxylic acid (7-01) (3 g, 7.28 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amine (8-a) (1.51 g, 8.01 mmol) in pyridine (40 mL) was added POCl3 (2 ml, 21.84 mol) at −10° C. The mixture was stirred at 0° C. for 2 h. After completion of the reaction, ice cooled-water (30 mL) was added to the reaction mixture at 0° C. The mixture was extracted with ethyl acetate (4×200 mL). The separated organic part was washed with saturated aqueous solution of NaHCO3, dried and concentrated to get a crude product which was purified by normal silica column using 40% ethyl acetate in hexane to get 5-benzyloxy-2-biphenyl-2-ylmethyl-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]methyl-amide (9-01) (2.1 g, 49.4%) as a yellow sticky mass.

Workup

  1. customAfter completion of the reaction, ice
  2. additionwas added to the reaction mixture at 0° C
  3. extractionThe mixture was extracted with ethyl acetate (4×200 mL)
  4. washThe separated organic part was washed with saturated aqueous solution of NaHCO3
  5. customdried
  6. concentrationconcentrated
  7. customto get a crude product which
  8. customwas purified by normal silica column

Sources & evidence

ORD record
ord-8e71d837a041415f937139f8a43aca81
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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