Diisopropylethylamine → HCID 178457485, compound

HRID 2169217Notes

Reaction equation

HRID 2169217 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:25]([OH:27])=O)=[N:11][C:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[Cl:24])=[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.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[Si:55]([O:62][CH2:63][CH2:64][NH:65][CH:66]([CH3:68])[CH3:67])([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56]>O1CCCC1.O>[Si:55]([O:62][CH2:63][CH2:64][N:65]([CH:66]([CH3:68])[CH3:67])[C:25]([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[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[Cl:24])[N:11]=1)=[O:27])([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 57917054N-(2-((tert-butyldimethylsilyl)oxy)ethyl)propan-2-amineHCID 178524879HCID 178524879, compound

Product 1

HCID 178457485HCID 178457485, compoundYield 32.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 5-benzyloxy-2-(2,3-dichlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid (131) (5.5 g, 13.58 mmol) in tetrahydrofuran (70 mL) were added N,N-diisopropylethylamine (9.36 mL, 54.32 mmol) and T3P (17.3 mL, 27.16 mmol) followed by [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropyl-amine (8b) (5.89 g, 27.16 mmol) at room temperature. The mixture was heated at 65° C. for 4 h. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The separated organic part was dried and concentrated to get a crude product which was purified by a normal silica column using 10 to 20% ethyl acetate in hexane to obtain 5-benzyloxy-2-(2,3-dichlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]isopropylamide (132) (2.7 g, 32.8%) as a light yellow solid.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe separated organic part was dried
  4. concentrationconcentrated
  5. customto get a crude product which
  6. customwas purified by a normal silica column

Sources & evidence

ORD record
ord-7a2c1ee18b3e47a6a1e3d461207d6542
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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