Diethyl chlorophosphate → HCID 60035416, compound

HRID 2079578Notes

Reaction equation

HRID 2079578 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3[N:14]=[C:15]([CH3:26])[N:16]=[C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][OH:25])[CH2:20][CH2:19]4)[C:12]=3[C:11]([CH3:27])=[CH:10]2)=[C:4]([CH3:28])[CH:3]=1.[P:29](Cl)([O:34][CH2:35][CH3:36])([O:31][CH2:32][CH3:33])=[O:30]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:32]([O:31][P:29](=[O:30])([O:34][CH2:35][CH3:36])[O:25][CH2:24][CH:21]1[CH2:22][CH2:23][N:18]([C:17]2[C:12]3[C:11]([CH3:27])=[CH:10][N:9]([C:5]4[C:6]([CH3:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=4[CH3:28])[C:13]=3[N:14]=[C:15]([CH3:26])[N:16]=2)[CH2:19][CH2:20]1)[CH3:33]

Participants

5

Reactant 2

HCID 13139Diethyl chlorophosphateHCID 104785674-Piperidinemethanol, 1-(7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo(2,3-d)pyrimidin-4-yl)-

Product 1

HCID 60035416HCID 60035416, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, to a solution of {1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl}methanol (0.50 g) and 4-dimethylaminopyridine (0.55 g) in CH2Cl2 (50 mL) at 0° C. diethyl chlorophosphate (0.38 g) was added dropwise and the reaction is slowly heated up to room temperature. The reaction mixture is poured on ice-water and extracted with CH2Cl2. After the usual work-up the residue is purified over silica gel on a glass filter (eluent: CH2Cl2/MeOH=98:2) yielding product 3-017 (0.31 g).

Workup

  1. additionThe reaction mixture is poured on ice-water
  2. extractionextracted with CH2Cl2
  3. customAfter the usual work-up the residue is purified over silica gel on a glass
  4. filtrationfilter (eluent: CH2Cl2/MeOH=98:2)

Sources & evidence

ORD record
ord-9a34f2b3d0014cd9ac544a1a07aee2c6
Source dataset
uspto-grants-2011_04
Patent number
US07932259B2

Reaction notes

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