4-Methylpiperidin-4-ol → HCID 86623565, compound

HRID 1365414Notes

Reaction equation

HRID 1365414 reaction equation
[CH3:1][C:2]1([OH:8])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:9][C:10]1[N:11]=[C:12]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:13]2[S:18][C:17]([CH:19]=O)=[CH:16][C:14]=2[N:15]=1>>[Cl:9][C:10]1[N:11]=[C:12]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[C:13]2[S:18][C:17]([CH2:19][N:5]3[CH2:6][CH2:7][C:2]([CH3:1])([OH:8])[CH2:3][CH2:4]3)=[CH:16][C:14]=2[N:15]=1

Participants

3

Reactant 2

HCID 156491744-Methylpiperidin-4-olHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 86623565HCID 86623565, compound

Procedure

Reaction of 4-methyl-piperidin-4-ol with 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde 10 using standard reductive amination conditions yielded 1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-4-methyl-piperidin-4-ol, which was reacted with 2-aminopyrimidine-5-boronic acid in General Procedure A. Purification on silica yielded 382. 400 MHz 1H NMR CDCl3: 9.21 (s, 2H, 2×Ar): 7.19 (s, 1H, ArH); 5.17 (brs, NH2): 3.95 (t, 4H, 2×CH2, J=4.7 Hz); 3.80 (t, 4H, 2×CH2, J=4.7 Hz); 3.76 (s, 2H, CH2); 2.60-2.54 (m, 2H, CH2); 2.44 (t, 2H, CH2, J=10.9 Hz); 1.69-1.62 (m, 2H, CH2); 1.55 (d, 2H, CH2, J=16.1 Hz); 1.20 (s, 3H, Me); 1.12 (s, 1H, OH). LC-MS (m+1)=442.13

Sources & evidence

ORD record
ord-6bb5ebf8dd754aad9223208a20c46f9c
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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