3-(Chloromethyl)pyridine → HCID 86618426, compound

HRID 2262202Notes

Reaction equation

HRID 2262202 reaction equation
N1C2C(=C(C3N=[C:12]([N:22]4[CH2:27]COCC4)[C:13]4S[C:17](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=C(CCl)C=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][CH2:17][C:16]3[CH:27]=[N:22][CH:12]=[CH:13][CH:14]=3)=[CH:35][C:33]=2[N:34]=1

Participants

6

Reactant 3

HCID 183583-(Chloromethyl)pyridineHCID 46180605(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanolHCID 59593094HCID 59593094, compound

Product 1

HCID 86618426HCID 86618426, 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 3-picolyl chloride to give 4-(2-chloro-6-((pyridin-3-ylmethoxy)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine. Suzuki coupling of 4-(2-chloro-6-((pyridin-3-ylmethoxy)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine and 7 was carried out via General Procedure A. Purification using column chromatography gave 319. NMR: CDCl3: 3.90-3.94 (4 H, m, CH2), 4.08-4.13 (4 H, m, CH2), 4.68 (2 H, s, CH2), 4.88 (2 H, s, CH2), 7.30 (1 H, dd, J 7.79 and 4.87, Ar), 7.44 (1 H, s, Ar), 7.51 (1 H, t, J 8.14, Ar), 7.57 (1 H, d, J 8.20, Ar), 7.71 (1 H, d, J 7.79, Ar), 8.28 (1 H, d, J 7.35, Ar), 8.58 (1 H, dd, J 4.80 and 1.47, Ar), 8.63 (1 H, d, J 1.86, Ar) and 9.02 (1 H, s, Ar). MS: (ESI+): MH+ 459.16

Sources & evidence

ORD record
ord-0dc2774b489a46919848299364bc255f
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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