Diisopropylethylamine → HCID 178457480, compound

HRID 2169468Notes

Reaction equation

HRID 2169468 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:28](O)=[O:29])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Si:64]([O:71][CH2:72][CH2:73][NH:74][CH:75]([CH3:77])[CH3:76])([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65]>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[Si:64]([O:71][CH2:72][CH2:73][N:74]([CH:75]([CH3:77])[CH3:76])[C:28]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:14]([OH:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]=1)=[O:29])([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57917054N-(2-((tert-butyldimethylsilyl)oxy)ethyl)propan-2-amineHCID 178524873HCID 178524873, compound

Product 1

HCID 178457480HCID 178457480, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (437) (180 mg, 0.44 mmol) in dimethylformamide (5 mL), N,N-diisopropylethylamine (0.22 mL, 1.33 mmol), HATU (253.5 mg, 0.667 mmol), and [2-(tert-Butyl-dimethylsilanyloxy)-ethyl]-isopropyl-amine (8b) were added, then this reaction mixture was allowed to stir for 16 h at room temperature while silica thin layer chromatography was performed (50% ethyl acetate in hexane; Rf=0.5). The reaction was quenched with ice cold water (20 mL) and extracted with ethyl acetate (2×30 mL). The combined extracts were dried, concentrated under vacuo and the resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography using 30-40% ethyl acetate in hexane as gradient polarity mobile phase to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylicacid[2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (438) (160 mg, 60%) as a yellow gummy liquid.

Workup

  1. customThe reaction was quenched with ice cold water (20 mL)
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. customThe combined extracts were dried
  4. concentrationconcentrated under vacuo
  5. customthe resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography

Sources & evidence

ORD record
ord-a94b24e8323d4b7ab15a4f3fd275ac22
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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