Tributylstannane → 4-Chloro-2-(tributylstannyl)pyrimidine

HRID 2086582Notes

Reaction equation

HRID 2086582 reaction equation
[Li+].CC([N-]C(C)C)C.[CH2:9]([SnH:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12].Cl[C:23]1[N:28]=[C:27]([Cl:29])[CH:26]=[CH:25][N:24]=1>>[Cl:29][C:27]1[CH:26]=[CH:25][N:24]=[C:23]([Sn:13]([CH2:9][CH2:10][CH2:11][CH3:12])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:18][CH2:19][CH2:20][CH3:21])[N:28]=1

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 775312,4-DichloropyrimidineHCID 2724682Lithium diisopropylamide

Product 1

HCID 149763044-Chloro-2-(tributylstannyl)pyrimidineYield 44.7%

Procedure

Using the procedure described in Example 1, Step 1, use LDA, tributyltin hydride (10.8 g, 37.2 mmol) and 2,4-dichloropyrimidine (5.2 g, 34.9 mmol)) to obtain the desired compound (6.3 g). 1H NMR (CDCl3) δ8.52 (d, 1H), 7.18 (d, 1H), 1.58 (m, 6H), 1.30 (q, 6H), 1.18 (t, 6H), 0.86 (t, 9H).

Sources & evidence

ORD record
ord-045a67f12c2a436faa283aa005c05c93
Source dataset
uspto-grants-2004_04
Patent number
US06727254B2

Reaction notes

Loading…