Dimethylformamide → HCID 21883111, compound

HRID 722250Notes

Reaction equation

HRID 722250 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)O[CH2:7][CH2:8][C:9]1[C:17]2[C:16]([Cl:18])=[N:15][C:14]([NH:19]C(=O)C)=[N:13][C:12]=2[NH:11][CH:10]=1)(C)(C)C.Cl.Cl[CH2:37][C:38]1[C:43]([CH3:44])=[C:42]([O:45][CH3:46])[C:41]([CH3:47])=[CH:40][N:39]=1.[C:48]([O-])([O-])=O.[K+].[K+].C[N:55]([CH:57]=O)C.CCO[C:62]([CH3:64])=O.O>[Cl-].[Na+].O>[Cl:18][C:16]1[C:17]2[C:9]([CH2:8][CH2:7][NH:55][CH2:57][CH:62]([CH3:64])[CH3:48])=[CH:10][N:11]([CH2:37][C:38]3[C:43]([CH3:44])=[C:42]([O:45][CH3:46])[C:41]([CH3:47])=[CH:40][N:39]=3)[C:12]=2[N:13]=[C:14]([NH2:19])[N:15]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 116942582-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochlorideHCID 21883095HCID 21883095, compoundHCID 22728543Water ethylacetate

Product 1

HCID 21883111HCID 21883111, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of N-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl}-acetamide (344 mg, 0.70 mmol), 2-chloromethyl-4-methoxy-3,5-dimethyl-pyridine hydrochloride (175 mg, 0.77 mmol), K2CO3 (516 mg, 3.7 mmol) and DMF (3.0 mL) was stirred at rt overnight. Work-up (EtOAc/water; brine) afforded the title compound as an off-white solid which was used without further purification (516 mg, “115%”). HPLC Rt: 8.419 min. 1H-NMR (CDCl3): δ 8.20 (s, 1H), 7.95 (s, 1H), 7.55 (dd, 4H), 7.32 (m, 6H), 7.04 (s, 1H), 5.37 (s, 2H), 3.91 (t, 2H), 3.73 (s, 3H), 3.06 (t, 2H), 2.57 (s, 3H), 2.26 (s, 3H), 2.25 (s, 3H), 0.97 (s, 9H).

Sources & evidence

ORD record
ord-c8f65fdbb93147e4825bd7f1a491e94f
Source dataset
uspto-grants-2006_11
Patent number
US07138402B2

Reaction notes

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