1-Amino-2-propanol → N-(2-hydroxypropyl)-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide

HRID 882176Notes

Reaction equation

HRID 882176 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[C:18]([C:19]([OH:21])=O)=[CH:17][N:16]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:30][CH2:31][CH:32]([OH:34])[CH3:33].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[OH:34][CH:32]([CH3:33])[CH2:31][NH:30][C:19]([C:18]1[C:11]2[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:15][CH:14]=[N:13][C:12]=2[N:16]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:28])([CH3:27])[CH3:29])[CH:17]=1)=[O:21]

Participants

7

Reactant 5

HCID 41-Amino-2-propanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 896132804-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid

Product 1

HCID 89629896N-(2-hydroxypropyl)-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (2.00 g, 4.83 mmol) in THF (50 mL), was added 1-aminopropan-2-ol (543 mg, 7.23 mmol), EDCI (1.12 g, 5.84 mmol), HOBt (800 mg, 5.92 mmol) and DIPEA (2.48 g, 19.2 mmol). The reaction was stirred for 12 hours at 25° C. and then concentrated in vacuo and quenched by addition of water. The reaction was extracted with DCM (×3) and the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was purified by chromatography using silica gel, eluting with 33% ethyl acetate/petroleum ether. The product was collected and concentrated in vacuo to afford N-(2-hydroxypropyl)-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide as a yellow solid. LRMS (ESI) calc'd for C22H30N5O5Si [M+H]+: 472, found 472.

Workup

  1. concentrationconcentrated in vacuo
  2. customquenched by addition of water
  3. extractionThe reaction was extracted with DCM (×3)
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe reaction was purified by chromatography
  8. washeluting with 33% ethyl acetate/petroleum ether
  9. customThe product was collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45666dab55434e18b6236d1bd29e013c
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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