4-(Chloromethyl)pyridine → HCID 86618427, compound

HRID 2098778Notes

Reaction equation

HRID 2098778 reaction equation
N1C2C(=C(C3N=[C:12]([N:22]4[CH2:27][CH2:26]OCC4)[C:13]4SC(COC)=[CH:16][C:14]=4N=3)C=CC=2)C=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.N1C=CC(CCl)=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][CH2:16][C:14]3[CH:13]=[CH:12][N:22]=[CH:27][CH:26]=3)=[CH:35][C:33]=2[N:34]=1

Participants

6

Reactant 3

HCID 745714-(Chloromethyl)pyridineHCID 46180605(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanolHCID 59593094HCID 59593094, compound

Product 1

HCID 86618427HCID 86618427, 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 4-picolyl chloride to give 4-(2-chloro-6-((pyridin-4-ylmethoxy)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine. Suzuki coupling of 4-(2-chloro-6-((pyridin-4-ylmethoxy)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine and 7 was carried out via General Procedure A. Purification using column chromatography gave 320. NMR: CDCl3: 3.90-3.94 (4 H, m, CH2), 4.08-4.13 (4 H, m, CH2), 4.68 (2 H, s, CH2), 4.92 (2 H, s, CH2), 7.30 (2 H, d, J 5.81, Ar), 7.46 (1 H, s, Ar), 7.51 (1 H, t, J 8.14, Ar), 7.60 (1 H, d, J 8.20, Ar), 8.28 (1 H, d, J 7.32, Ar), 8.61 (2 H, d, J 5.27, Ar), 9.01 (1 H, s, Ar) and 10.14 (1 H, s, NH). MS: (ESI+): MH+ 459.17

Sources & evidence

ORD record
ord-9437d7e5f3e24df3af33880503531fae
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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