1,1,2-Trimethoxyethane → HCID 21217674, compound

HRID 1586010Notes

Reaction equation

HRID 1586010 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[F:20].[CH3:21][O:22][CH:23](OC)[CH2:24]OC>>[F:20][C:14]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=1[NH:12][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][CH2:24][CH2:23][O:22][CH3:21])[CH:3]=2)[N:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 475201,1,2-TrimethoxyethaneHCID 21217678N4-(2,4-Difluorophenyl)-4,6-quinazolinediamine

Product 1

HCID 21217674HCID 21217674, compoundYield 28%

Procedure

Using an analogous reductive amination procedure to that described in Example 1, 6-amino-4-(2',4'-difluoroanilino)quinazoline was reacted with 2-methoxyacetaldehyde dimethyl acetal to give 4-(2',4'-difluoroanilino)-6-(2-methoxyethylamino)quinazoline in 28% yield, m.p. 175-176° C.; NMR Spectrum: 3.31 (s, 3H), 3.38 (t, 2H), 3.61 (t, 2H), 6.19 (t, 1H), 7.07-7.18 (m, 2H), 7.27-7.38 (m, 2H), 7.48-7.6 (m, 2H), 8.2 (s, 1H), 9.3 (broad s, 1H); Elemental Analysis: Found C, 61.7; H, 4.9; N, 16.9; C17H16F2N4O requires C, 61.8; H, 4.9; N, 17.0%.

Sources & evidence

ORD record
ord-814083dc65684eabacc7a3da962dd485
Source dataset
uspto-grants-1999_08
Patent number
US05942514

Reaction notes

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