Benzyl Bromide → HCID 86618423, compound

HRID 2262199Notes

Reaction equation

HRID 2262199 reaction equation
N1[C:9]2[C:4](=[C:5](C3N=C(N4CCOCC4)C4SC(COC)=CC=4N=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=N1.[Cl:28][C:29]1[N:30]=[C:31]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[C:32]2[S:37][C:36]([CH2:38][OH:39])=[CH:35][C:33]=2[N:34]=1.C(Br)C1C=CC=CC=1>CN(C=O)C.[H-].[Na+]>[Cl:28][C:29]1[N:30]=[C:31]([N:40]2[CH2:41][CH2:42][O:43][CH2:44][CH2:45]2)[C:32]2[S:37][C:36]([CH2:38][O:39][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:35][C:33]=2[N:34]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 46180605(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanolHCID 59593094HCID 59593094, compound

Product 1

HCID 86618423HCID 86618423, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24758Sodium hydrideSolvent

Procedure

Following the procedures for compound 314, (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-methanol in DMF and sodium hydride was alkylated with benzyl bromide to give 2-chloro-6-benzyloxymethyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine. Suzuki coupling of 2-chloro-6-benzyloxymethyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine and 7 was carried out via General Procedure A. Purification using column chromatography gave 315. NMR: CDCl3: 3.88-3.94 (4 H, m, CH2), 4.09-4.14 (4 H, m, CH2), 4.69 (2 H, s, CH2), 4.86 (2 H, s, CH2), 7.31-7.46 (6 H, m, Ar), 7.53 (1 H, t, J 8.22, Ar), 7.56 (1 H, t, J 8.24, Ar), 8.30 (1 H, d, J 6.94, Ar), 9.03 (1 H, s, Ar) and 10.1 (1 H, s, NH). MS: (ESI+): MH+ 458.16

Sources & evidence

ORD record
ord-2a9e1d147174480b823f7c40628f5b02
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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