Chloroacetyl chloride → HCID 131734745, compound

HRID 1775752Notes

Reaction equation

HRID 1775752 reaction equation
[C:1]([Si:5]([CH3:36])([CH3:35])[O:6][CH2:7][CH:8]1[O:12][CH:11]([N:13]2[CH:18]=[C:17]3[CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:24][CH:23]=4)[O:21][C:16]3=[N:15][C:14]2=[O:33])[CH2:10][CH:9]1[OH:34])([CH3:4])([CH3:3])[CH3:2].[Cl:37][CH2:38][C:39](Cl)=[O:40]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:37][CH2:38][C:39]([O:34][C@H:9]1[CH2:10][C@H:11]([N:13]2[CH:18]=[C:17]3[CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:24][CH:23]=4)[O:21][C:16]3=[N:15][C:14]2=[O:33])[O:12][C@@H:8]1[CH2:7][O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:36])[CH3:35])=[O:40]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 67121724HCID 67121724, compound

Product 1

HCID 131734745HCID 131734745, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 25 mL flask was added 102 mg (0.2 mmol) of 3-(5-((tert-butyldimethyl silyloxy)methyl)-4-hydroxy-tetrahydrofuran-2-yl)-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-2(3H)-one, 48 mg (0.4 mmol) of DMAP, and 5 mL of DCM. 30 μl (0.4 mmol) of chloroacetyl chloride was added dropwise. The mixture was stirred at rt for 1 h.

Sources & evidence

ORD record
ord-2fc6492dc2704080aad2d16e91919864
Source dataset
uspto-grants-2016_02
Patent number
US09260469B2

Reaction notes

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