2-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde → HCID 57494055, compound

HRID 881546Notes

Reaction equation

HRID 881546 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1([OH:12])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[Cl:13][C:14]1[N:15]=[C:16]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:17]2[S:22][C:21]([CH:23]=O)=[CH:20][C:18]=2[N:19]=1>>[Cl:13][C:14]1[N:15]=[C:16]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[C:17]2[S:22][C:21]([CH2:23][N:9]3[CH2:8][CH2:7][C:6]([C:2]4[S:1][CH:5]=[CH:4][N:3]=4)([OH:12])[CH2:11][CH2:10]3)=[CH:20][C:18]=2[N:19]=1

Participants

3

Reactant 2

HCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehydeHCID 57420365HCID 57420365, compound

Product 1

HCID 57494055HCID 57494055, compound

Procedure

Reaction of 4-thiazol-2-yl-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-thiazol-2-yl-piperidin-4-ol, which was reacted with 2-aminopyrimidine-5-boronic acid in General Procedure A. Purification on silica yielded 408. 400 MHz 1H NMR CDCl39.30 (s, 2H); 7.76 (d, 1H, J=3.3 Hz); 7.325 (d, 1H, J=3.3 Hz); 7.31 (s, 1H); 5.23 (s, NH2); 4.07-3.90 (m, 8H); 2.92 (d, 2H, J=11.7 Hz); 2.66 (t, 2H); 2.36 (m, 2H); 1.95 (d, 2H, J=11.6 Hz). LC-MS (m+1)=511.14

Sources & evidence

ORD record
ord-16b0678327424af09b3df18d8e804d58
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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