Triethylamine → HCID 67523859, compound

HRID 659023Notes

Reaction equation

HRID 659023 reaction equation
[Si:1](Cl)([C:4](C)(C)C)([CH3:3])[CH3:2].[NH2:9][C:10]1[CH:27]=[CH:26][C:13]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][CH2:23][CH2:24][OH:25])[N:16]=2)=[CH:12][CH:11]=1.C(N(CC)CC)C>ClCCl>[NH2:9][C:10]1[CH:27]=[CH:26][C:13]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][CH2:23][CH2:24][O:25][Si:1]([CH3:2])([CH3:3])[CH3:4])[N:16]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 67524085HCID 67524085, compound

Product 1

HCID 67523859HCID 67523859, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.99 ml (1.99 mmol) of 1M t-butyl-dimethylsilyl chloride in dichloromethane were added at 0° C. to a solution of 470 mg (1.81 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol and 256 mg (2.53 mmol) triethylamine in 5 ml dichloromethane. The reaction mixture was stirred for 12 h at r.t. and extracted with water. The organic phase was dried (sodium sulphate) and evaporated. The obtained material was purified by chromatography on silica (ethyl acetate/n-heptane 1:1) to give 520 mg (77%) oily [4-(4-Amino-phenoxy)-pyrimidin-2-yl]-(3-trimethylsilanyloxy-propyl)-amine.

Workup

  1. extractionextracted with water
  2. dry with materialThe organic phase was dried (sodium sulphate)
  3. customevaporated
  4. customThe obtained material was purified by chromatography on silica (ethyl acetate/n-heptane 1:1)

Sources & evidence

ORD record
ord-9748bb19ec76400caaea32e2a87bbe63
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

Loading…