Diisopropylethylamine → HCID 178455268, compound

HRID 2169381Notes

Reaction equation

HRID 2169381 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:32]([OH:34])=O)=[N:11][C:12]([CH2:16][C:17]2([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH: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.[Si:44]([O:51][CH2:52][CH2:53][NH2:54])([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[Si:44]([O:51][CH2:52][CH2:53][NH:54][C:32]([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[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:19][CH2:20][CH2:21]2)[N:11]=1)=[O:34])([C:47]([CH3:49])([CH3:50])[CH3:48])([CH3:46])[CH3:45]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524864HCID 178524864, compound

Product 1

HCID 178455268HCID 178455268, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (345) (250 mg, 0.55 mmol) in dimethylformamide (7.5 mL) were added N,N-diisopropylethylamine (0.27 mL, 1.65 mmol), 2-(tert-butyl-dimethylsilanyloxy)-ethylamine (8c) (145 mg, 0.83 mmol) and HATU (251 mg, 0.66 mmol) and the reaction mixture was stirred at room temperature for 1.5 h (silica TLC, 50% ethyl acetate in hexane, Rf=0.5). The reaction mass was diluted with ethyl acetate (60 ml) and washed with brine (3×30 mL). The organic phase was thereafter dried and concentrated in vacuo to get a crude mass which was purified by CombiFlash using a gradient eluent mixture of ethyl acetate and hexane to get pure 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-amide (346) (315 mg, 94%) as a white solid.

Workup

  1. washwashed with brine (3×30 mL)
  2. customThe organic phase was thereafter dried
  3. concentrationconcentrated in vacuo
  4. customto get a crude mass which
  5. customwas purified by CombiFlash
  6. additiona gradient eluent mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c508c2efa8494072b88d919d659fa669
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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