2,4-Diamino-5-pyrimidinemethanol → HCID 23323034, compound

HRID 279975

Reaction equation

HRID 279975 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[NH:14][CH2:13][CH2:12][CH2:11]2.[NH2:16][C:17]1[N:22]=[C:21]([NH2:23])[C:20]([CH2:24]O)=[CH:19][N:18]=1>>[NH2:16][C:17]1[N:22]=[C:21]([NH2:23])[C:20]([CH2:24][C:8]2[CH:9]=[C:10]3[C:15](=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=2)[NH:14][CH2:13][CH2:12][CH2:11]3)=[CH:19][N:18]=1

Participants

3

Reactant 2

HCID 2958782,4-Diamino-5-pyrimidinemethanolHCID 23323055HCID 23323055, compound

Product 1

HCID 23323034HCID 23323034, compound

Procedure

The procedure of Example 1 was used to react 1,2,3,4-tetrahydro-8-methoxyethoxyquinoline (3.11 g) with 2,4-diamino-5-hydroxymethylpyrimidine, and 2,4-diamino-5-(1,2,3,4-tetrahydro-8-(2-methoxyethoxy)-6-quinolylmethyl)pyrimidine was isolated and purified as in this example. The free base was recrystallized from absolute ethanol; m.p. 149°-151° C. NMR (Me2SO-d6) δ 1.76 (m, 2, CH2), 2.61 (tr, 2, CH2), 3.22 (m, 2, CH2), 3.31 (s, 3, OMe), 3.39 (s, 2, bridge CH2), 3.65 (m, 2, CH2CH2O), 3.97 (m, 2, OCH2CH2), 4.60 (br. s., 1, NH), 5.60 and 5.90 (2 br s, 4, (NH2)2), 6.36 (d, 1, J=1-2, Ar), 6.53 (d, 1, J=1- 2, Ar), 7.45 (s, 1, pyrimidine-6-H). Anal. Calcd. for C17H23N5O2 : C, 61.99; H, 7.04; N, 21.26. Found: C, 61.82; H, 7.06; N, 21.25.

Sources & evidence

ORD record
ord-53dcb0a0e2b740db96ab761486bfae7b
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Linked notes

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