Tetrahydrofuran → HCID 21883111, compound

HRID 722251Notes

Reaction equation

HRID 722251 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([Cl:25])[C:5]2[C:10]([CH2:11][CH2:12]O)=[CH:9][N:8]([CH2:14][C:15]3[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[C:18]([CH3:24])=[CH:17][N:16]=3)[C:6]=2[N:7]=1.C[CH2:27][N:28](CC)CC.CS(Cl)(=O)=O.[CH2:38]1[CH2:42]OC[CH2:39]1>>[Cl:25][C:4]1[C:5]2[C:10]([CH2:11][CH2:12][NH:28][CH2:27][CH:38]([CH3:39])[CH3:42])=[CH:9][N:8]([CH2:14][C:15]3[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[C:18]([CH3:24])=[CH:17][N:16]=3)[C:6]=2[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11199248HCID 11199248, compound

Product 1

HCID 21883111HCID 21883111, compound

Procedure

A solution of 2-[2-amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-ethanol (11.6 mg, 0.031 mmol) and Et3N (30 ul, 0.22 mmol) in THF (2 mL) was treated with MsCl (11 uL, 0.14 mmol) at rt for 15 min to give a solution of the title compound which was used without further purification. In a separate experiment, the material was purified by preparative TLC (EtOAc 100%). HPLC Rt: 4.765 min. 1H-NMR (CDCl3): δ 8.22 (s, 1H), 6.80 (s, 1H), 5.31 (s, 2H), 4.93 (s, 2H), 4.42 (t, 2H), 3.77 (s, 3H), 2.98 (t, 2H), 2.85 (s, 3H), 2.23 (s, 3H), 2.07 (s, 3H).

Sources & evidence

ORD record
ord-645cbab8689341a99de975a45c4c43d6
Source dataset
uspto-grants-2006_11
Patent number
US07138402B2

Reaction notes

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