Methyl iodide → HCID 11438229, compound

HRID 2105124Notes

Reaction equation

HRID 2105124 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([C:14]2[N:22]3[C:17]([CH2:18][O:19][CH2:20][CH2:21]3)=[N:16][CH:15]=2)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([Li])CCC.IC>CCCCCC>[NH:1]([C:8]1[N:13]=[C:12]([C:14]2[N:22]3[C:17]([CH:18]([CH3:23])[O:19][CH2:20][CH2:21]3)=[N:16][CH:15]=2)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11437818HCID 11437818, compoundHCID 178418339Butyllithium

Product 1

HCID 11438229HCID 11438229, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

By an analogous process to Example 10, 2-Anilino-4-(5,6-dihydro-8H-imidazo[2,1-c][1,4]oxazin-3-yl)pyrimidine (Example 5; 163 mg, 0.556 mmol) was treated with n-butyllithium (0.73 ml of a 1.6M solution in hexane, 1.168 mmol) and iodomethane (36 μl, 0.583 mmol) to give the title compound (67 mg, 39%) as a pale yellow solid. NMR: 1.5 (d, 3H), 3.9 (m, 1H), 4.18 (m, 1H), 4.32 (m, 1H), 4.63 (m, 1H), 4.87 (q, 1H), 6.95 (t, 1H), 7.13 (d, 1H), 7.3 (t, 2H), 7.67 (d, 2H), 7.75 (s, 1H), 8.37 (d, 1H), 9.4 (s, 1H); m/z 308.

Sources & evidence

ORD record
ord-290cbf8f31304d6f9d126a33ff43c380
Source dataset
uspto-grants-2009_08
Patent number
US07579344B2

Reaction notes

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